- Room-temperature Pd-catalyzed methoxycarbonylation of terminal alkynes with high branched selectivity enabled by bisphosphine-picolinamide ligand
-
We report the room-temperature Pd-catalyzed methoxy-carbonylation with high branched selectivity using a new class of bisphosphine-picolinamide ligands. Systematic optimization of ligand structures and reaction conditions revealed the significance of both
- Chen, Fen-Er,Ke, Miaolin,Liu, Ding,Ning, Yingtang,Ru, Tong
-
p. 1041 - 1044
(2022/01/28)
-
- The total synthesis of (-) -strempeliopine: Via palladium-catalyzed decarboxylative asymmetric allylic alkylation
-
In the work reported herein, the concise and enantioselective total synthesis of the Schizozygine alkaloid (-)-strempeliopine was developed. This synthetic strategy featured the palladium-catalyzed decarboxylative asymmetric allylic alkylation of N-benzoy
- An, Yi,Chen, Fener,Li, Weijian,Li, Yaling,Tang, Pei,Wang, Zhenzhen,Wu, Mengjuan,Xue, Yansong
-
p. 1402 - 1405
(2022/02/09)
-
- Amino alcohols using the optically active amino alcohol derivative bi- Nord complex boron - -
-
Disclosed are an amino alcohol-boron-binol complex as an intermediate, including Complex 3-1-1 shown below, and a method for preparing an optically active amino alcohol by using the same, wherein a racemic amino alcohol is resolved in an enationselective manner using a boron compound and a (R)- or (S)-binol, whereby an amino alcohol derivative with high optical purity can be prepared at high yield.
- -
-
Paragraph 0064; 0071-0076; 0281-0283; 0285-0286
(2021/04/16)
-
- Method for synthesizing venlafaxine by utilizing fixed bed hydrogenation equipment
-
The invention discloses a method for synthesizing venlafaxine by using fixed bed hydrogenation equipment, which comprises the following step: weighing methoxybenzyl cyanide and cyclohexanone as raw materials, and preparing an intermediate 1 under the action of sodium hydroxide. According to the method for synthesizing venlafaxine by using the fixed bed hydrogenation equipment, sodium hydroxide is used as alkali to produce the intermediate 1, so that ultra-low temperature and use of an active reagent are avoided, the production technical difficulty is reduced, a filled supported precious metal catalyst is adopted to carry out catalytic hydrogenation reaction, the intermediate 1 and hydrogen carry out reduction under the action of a catalyst loaded on one ore more of rhodium, palladium, and nickel, a cyan group of the intermediate 1 molecule is reduced into an amino group,venlafaxine is synthesized through fixed bed hydrogenation equipment, a supported catalyst is filled into a stainless steel reaction tube of the fixed bed hydrogenation equipment, the reactions can be carried out continuously, and the method has the characteristics of small reaction volume, large yield, safe production, and low production cost.
- -
-
Paragraph 0031-0090
(2021/06/09)
-
- Simple RuCl3-catalyzed N-Methylation of Amines and Transfer Hydrogenation of Nitroarenes using Methanol
-
Methanol is a potential hydrogen source and C1 synthon, which finds interesting applications in both chemical synthesis and energy technologies. The effective utilization of this simple alcohol in organic synthesis is of central importance and attracts scientific interest. Herein, we report a clean and cost-competitive method with the use of methanol as both C1 synthon and H2 source for selective N-methylation of amines by employing relatively cheap RuCl3.xH2O as a ligand-free catalyst. This readily available catalyst tolerates various amines comprising electron-deficient and electron-donating groups and allows them to transform into corresponding N-methylated products in moderate to excellent yields. In addition, few marketed pharmaceutical agents (e. g., venlafaxine and imipramine) were also successfully synthesized via late-stage functionalization from readily available feedstock chemicals, highlighting synthetic value of this advanced N-methylation reaction. Using this platform, we also attempted tandem reactions with selected nitroarenes to convert them into corresponding N-methylated amines using MeOH under H2-free conditions including transfer hydrogenation of nitroarenes-to-anilines and prepared drug molecules (e. g., benzocaine and butamben) as well as key pharmaceutical intermediates. We further enable one-shot selective and green syntheses of 1-methylbenzimidazole using ortho-phenylenediamine (OPDA) and methanol as coupling partners.
- Sarki, Naina,Goyal, Vishakha,Tyagi, Nitin Kumar,Puttaswamy,Narani, Anand,Ray, Anjan,Natte, Kishore
-
p. 1722 - 1729
(2021/04/19)
-
- Bisguanidinium-Catalyzed Epoxidation of Allylic and Homoallylic Amines under Phase Transfer Conditions
-
A highly enantioselective epoxidation reaction of allylic and homoallylic amines has been disclosed using an ion pair catalyst, which consists of chiral cationic bisguanidinium [BG]2+ and an achiral tetraperoxyditungstate anion [W2O2(μ-O)(O2)4]2-. The terminal oxidant is a stoichiometric amount of aqueous hydrogen peroxide, an environmentally benign reagent. Up to 96% enantiomeric excess and 99% yields were achieved for 1,1′-disubstituted and 1,2-disubstituted allylic protected amines and 1,2-disubstituted homoallylic protected amines. The identity of the ion pair catalyst was uncovered using X-ray crystallography and revealed that the achiral tetraperoxyditungstate anion species [W2O2(μ-O)(O2)4]2- is nudged nicely into the central cavity of the chiral dication. The ion pair catalyst was also characterized using infrared (IR) and Raman spectroscopies. The synthesis of (-)-venlafaxine was achieved via this reported methodology to demonstrate its usefulness.
- Chin, Kek Foo,Kabylda, Adil M.,Lee, Richmond,Leow, Dasheng,Li, Yongxin,Tan, Choon-Hong,Xia Ang, Esther Cai,Ye, Xinyi,Zhang, Xin
-
p. 2684 - 2691
(2020/03/11)
-
- Enantioseparation of chiral pharmaceuticals by vancomycin-bonded stationary phase and analysis of chiral recognition mechanism
-
The drug chirality is attracting increasing attention because of different biological activities, metabolic pathways, and toxicities of chiral enantiomers. The chiral separation has been a great challenge. Optimized high-performance liquid chromatography (HPLC) methods based on vancomycin chiral stationary phase (CSP) were developed for the enantioseparation of propranolol, atenolol, metoprolol, venlafaxine, fluoxetine, and amlodipine. The retention and enantioseparation properties of these analytes were investigated in the variety of mobile phase additives, flow rate, and column temperature. As a result, the optimal chromatographic condition was achieved using methanol as a main mobile phase with triethylamine (TEA) and glacial acetic acid (HOAc) added as modifiers in a volume ratio of 0.01% at a flow rate of 0.3?mL/minute and at a column temperature of 5°C. The thermodynamic parameters (eg, ΔH, ΔΔH, and ΔΔS) from linear van 't Hoff plots revealed that the retention of investigated pharmaceuticals on vancomycin CSP was an exothermic process. The nonlinear behavior of lnk′ against 1/T for propranolol, atenolol, and metoprolol suggested the presence of multiple binding mechanisms for these analytes on CSP with variation of temperature. The simulated interaction processes between vancomycin and pharmaceutical enantiomers using molecular docking technique and binding energy calculations indicated that the calculated magnitudes of steady combination energy (ΔG) coincided with experimental elution order for most of these enantiomers.
- Li, Jiaxi,Liu, Ruixia,Wang, Liyang,Liu, Xiaoling,Gao, Hongjie
-
p. 236 - 247
(2019/02/01)
-
- A method for preparing venlafaxine hydrochloride (by machine translation)
-
The invention provides a preparation method of venlafaxine hydrochloride, comprises the following steps: in the borohydride and of Lewis acids in reduction system under I compound formula II compound suitcase; the formula II compound acid formation to get to the venlafaxine hydrochloride; according to the present invention provides a preparation method of venlafaxine hydrochloride, the reaction process is safe, easy to control, and the cost is low, the ideal result, is suitable for industrial production. (by machine translation)
- -
-
Paragraph 0036; 0037; 0039; 0040; 0042; 0043
(2019/04/10)
-
- Preparation method of demethylvenlafaxine succinate compound
-
The invention discloses a preparation method of a demethylvenlafaxine succinate compound. The preparation method is characterized in that 1-[2-amino-1-(4-methoxyphenyl)ethyl] cyclohexanol hydrochloride is taken as an initial material to prepare a demethylvenlafaxine succinate compound finished product with high purity by virtue of two-step reaction of methylation and demethylation as well as the reaction with succinic acid in a mixed solvent of acetone-water. The improved process is high in yield, low in cost, easy in operation and beneficial to the industrialized production.
- -
-
Paragraph 0027; 0045; 0046; 0049
(2019/05/02)
-
- Efficient resolution of venlafaxine and mechanism study via X-ray crystallography
-
Numbers of resolving factors were investigated to improve resolution of venlafaxine 1. An effective resolving agent, O,O′-di-p-toluoyl-(R, R)-tartaric acid 2, was screened using similar method of ‘Dutch resolution’ from tartaric acid derivatives. The resolution efficiency was up to 88.4%, when the ratio of rac-1 and 2 was 1:0.8 in THF with little water (10:1?v/v). Enantiomerically pure venlafaxine was prepared with 99.1% ee in 82.2% yield. The chiral resolution mechanism was first explained through X-ray crystallographic study. One diastereomeric salt with well solubility forms a columnar supramolecular structure as the acidic salt (R)-1·2, while the other diastereomeric salt with less solubility forms a multilayered sandwich supramolecular structure by enantio-differentiation self-assembly as the neutral salt 2(S)-1·2. The water molecules play a key role in the optical resolution, as indicated by the special structures of the diastereomeric salts.
- Liu, Zhi-Jin,Liu, Han,Chen, Xuan-Wen,Lin, Min,Hu, Yu,Tuo, Xun,Yuan, Zhong-Yi,Sun, Xiao-Xia
-
p. 268 - 274
(2018/02/19)
-
- Expedient Synthesis of N-Methyl- and N-Alkylamines by Reductive Amination using Reusable Cobalt Oxide Nanoparticles
-
N-Methyl- and N-alkylamines represent important fine and bulk chemicals that are extensively used in both academic research and industrial production. Notably, these structural motifs are found in a large number of life-science molecules and play vital roles in regulating their activities. Therefore, the development of convenient and cost-effective methods for the synthesis and functionalization of amines by using earth-abundant metal-based catalysts is of scientific interest. In this regard, herein we report an expedient reductive amination process for the selective synthesis of N-methylated and N-alkylated amines by using nitrogen-doped, graphene-activated nanoscale Co3O4-based catalysts. Starting from inexpensive and easily accessible nitroarenes or amines and aqueous formaldehyde or aldehydes in the presence of formic acid, this cost-efficient reductive amination protocol allows the synthesis of various N-methyl- and N-alkylamines, amino acid derivatives, and existing drug molecules.
- Senthamarai, Thirusangumurugan,Murugesan, Kathiravan,Natte, Kishore,Kalevaru, Narayana V.,Neumann, Helfried,Kamer, Paul C. J.,Jagadeesh, Rajenahally V.
-
p. 1235 - 1240
(2018/02/09)
-
- Application of Unusual Grignard Reaction for the Stereoselective Synthesis of Antidepressant Drug (R)-(-)-Venlafaxine
-
An enantioselective synthesis of antidepressant drug (R)-(-)-venlafaxine is accomplished as an application of recently explored unusual Grignard reaction. An innovative method for the generation of chirality at extremely reactive benzylic center along with determination of absolute stereochemistry has been discussed. The key steps involved in the synthesis include Sharpless asymmetric dihydroxylation for the induction of chirality and an unusual Grignard reaction.
- Chavan, Subhash P.,Khatod, Harshali S.
-
p. 1410 - 1418
(2017/03/11)
-
- Selective Hydrogenation of Nitriles to Primary Amines Catalyzed by a Polysilane/SiO2-Supported Palladium Catalyst under Continuous-Flow Conditions
-
Hydrogenation of nitriles to primary amines with heterogeneous catalysts under liquid-phase continuous-flow conditions is described. Newly developed polysilane/SiO2-supported Pd was found to be an effective catalyst and various nitriles were converted into primary amine salts in almost quantitative yields under mild reaction conditions. Interestingly, a complex mixture was obtained under batch conditions. Lifetime experiments showed that this catalyst remained active for more than 300 h (TON≥10 000) without loss of selectivity and no metal leaching from the catalyst occurred. By using this continuous-flow hydrogenation, synthesis of venlafaxine, an antidepressant drug, has been accomplished.
- Saito, Yuki,Ishitani, Haruro,Ueno, Masaharu,Kobayashi, Shū
-
p. 211 - 215
(2017/04/21)
-
- NOVEL PROCESS FOR TOTAL SYNTHESIS OF VENLAFAXINE
-
There is a need for short, resolution free asymmetric process for synthesis of one isomer of venlafaxine, (-)-venlafaxine. The invention provides a novel, short process of synthesis of (-)-venlafaxine, with yield greater than 50% and ee> 99%. This process can be used for racemic synthesis of venlafaxine with overall yield 65%.
- -
-
-
- ASYMMETRIC SYNTHESIS OF (-)-VENLAFAXINE USING ORGANOCATALYST
-
The patent discloses an asymmetric synthesis of (?)-venlafaxine using an organocatalyst via a unified strategy employing organcatalytic Michael addition, regio-selective dehydration and selective epoxide ring opening.
- -
-
-
- DERIVATIVES OF (-)-VENLAFAXINE AND METHODS OF PREPARING AND USING THE SAME
-
Methods of preparing, and compositions comprising, derivatives of (?)-venlafaxine are disclosed. Also disclosed are methods of treating and preventing diseases and disorders including, but not limited to, affective disorders such as depression, bipolar and manic disorders, attention deficit disorder, attention deficit disorder with hyperactivity, Parkinson's disease, epilepsy, cerebral function disorders, obesity and weight gain, incontinence, dementia and related disorders.
- -
-
-
- Venlafaxine assay
-
The invention describes antibodies that bind venlafaxine and O-desmethylvenlafaxine. The antibodies are derived from novel haptens and immunogens and are used in methods and kits to detect and quantify venlafaxine and O-desmethylvenlafaxine. The invention also describes novel detecting agents which can be used in the methods and kits of the invention.
- -
-
Page/Page column
(2015/08/03)
-
- ASYMMETRIC SYNTHESIS OF (-)-VENLAFAXINE USING ORGANOCATALYST
-
The patent discloses an asymmetric synthesis of (-)-venlafaxine using an organocatalyst via a unified strategy employing organcatalytic Michael addition, regio-selective dehydration and selective epoxide ring opening.
- -
-
-
- A protecting group free and scalable approach towards total synthesis of (-)-venlafaxine
-
A protecting group free asymmetric total synthesis of (-)-venlafaxine is reported. The strategy employs Sharpless epoxidation and regio-selective epoxide ring opening by an in situ generated Gilman reagent as key steps. This paper reports a 53% overall yield in 6 steps for total synthesis of (-)-venlafaxine. This journal is the Partner Organisations 2014.
- Chavan, Subhash P.,Pawar, Kailash P.,Garai, Sumanta
-
p. 14468 - 14470
(2014/04/17)
-
- General catalytic methylation of amines with formic acid under mild reaction conditions
-
A general catalytic protocol for the methylation of amines has been developed applying, for the first time, formic acid as the C1 building block and silanes as reducing agents. A broad range of aromatic and aliphatic, both primary and secondary, amines has been converted to the corresponding tertiary amines including [N-13C]-labelled drugs in good to excellent yields under mild conditions. Methylation made easy: A general catalytic protocol for the methylation of amines has been developed applying, for the first time, formic acid as the C1 building block and silanes as reducing agents. A broad range of aromatic and aliphatic, both primary and secondary, amines has been converted to the corresponding tertiary amines, including [N-13C]-labelled drugs, in good to excellent yields at mild conditions (see scheme; dppp=(1,3-bis(diphenylphosphino)propane)).
- Sorribes, Ivan,Junge, Kathrin,Beller, Matthias
-
supporting information
p. 7879 - 7883
(2014/07/07)
-
- Venlafaxine Assay
-
The invention describes antibodies that bind venlafaxine and O-desmethylvenlafaxine. The antibodies are derived from novel haptens and immunogens and are used in methods and kits to detect and quantify venlafaxine and O-desmethylvenlafaxine. The invention also describes novel detecting agents which can be used in the methods and kits of the invention.
- -
-
Page/Page column
(2014/06/11)
-
- Asymmetric total synthesis of (-)-venlafaxine using an organocatalyst
-
An asymmetric total synthesis of (-)-venlafaxine using an organocatalyst has been achieved via a unified strategy employing organcatalytic Michael addition, regio-selective dehydration and selective epoxide ring opening.
- Chavan, Subhash P.,Garai, Sumanta,Pawar, Kailash P.
-
p. 2137 - 2139
(2013/05/21)
-
- Asymmetric synthesis of both the enantiomers of antidepressant venlafaxine and its analogues
-
Chemoenzymatic asymmetric synthesis of antidepressant agent venlafaxine and its analogue have been reported in this communication. The main highlight of the reported synthesis is the stereoselective synthesis of cyanohydrins by (S)-hydroxynitrile lyase (Hevea brasiliensis) followed by lipase catalyzed kinetic resolution.
- Bhuniya, Rajib,Nanda, Samik
-
scheme or table
p. 1990 - 1992
(2012/05/05)
-
- POLYMORPHIC FORMS OF O-DESMETHYL-VENLAFAXINE SUCCINATE FIELD OF THE INVENTION
-
The present invention discloses polymorphic forms of O-desmethyl-venlafaxine succinate and processes for the preparation thereof.
- -
-
Page/Page column 17; 18
(2012/04/23)
-
- POLYMORPHIC FORMS OF O-DESMETHYL-VENLAFAXINE SUCCINATE
-
The present invention discloses polymorphic forms of O-desmethyl-venlafaxine succinate and processes for the preparation thereof.
- -
-
Page/Page column 7
(2012/10/23)
-
- An improved and impurity-free large-scale synthesis of venlafaxine hydrochloride
-
An improved and impurity-free synthetic method for large-scale synthesis of venlafaxine hydrochloride was developed using inexpensive reagents. The overall yield obtained from this newly developed process is 55% in a highly pure state with >99.9% purity by HPLC.
- Saravanan, Mohanarangam,Satyanarayana, Bollikonda,Reddy, Padi Pratap
-
p. 1392 - 1395
(2012/01/13)
-
- A chemoselective deoxygenation of N-oxides by sodium borohydride-Raney nickel in water
-
A simple and convenient protocol for deoxygenation of aliphatic and aromatic N-oxides to the corresponding amines in good to excellent yield using sodium borohydride-Raney nickel in water is reported. Other functional moieties such as alkenes, halides, ethers, and amides are unaffected under the present reaction condition.
- Gowda, Narendra B.,Rao, Gopal Krishna,Ramakrishna, Ramesha A.
-
experimental part
p. 5690 - 5693
(2010/11/05)
-
- N-OXIDES OF VENLAFAXINE AND O-DESMETHYLVENLAFAXINE AS PRODRUGS
-
Embodiments of the invention relate to a compound of formula (1), or a tautomer, stereoisomer, hydrate, or solvate thereof, wherein R1 is H or CH3. Other embodiments of the invention relate to a pharmaceutical composition containing these compound, to methods for preparing these compounds, and to methods for preparing compositions containing these compounds. Yet other embodiments of the invention relate to the uses of these compounds and compositions containing it, such as for the manufacture of medicaments and pharmaceutical compositions for treating a condition chosen from depression, major depressive disorder, generalized anxiety disorder, obsessive compulsive disorder, social anxiety disorder, panic disorder, general depressive disorders, diabetic neuropathy, migraine and hot flashes.
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-
Page/Page column 7
(2009/01/24)
-
- Preparation of phenethyl tertiary amine derivatives
-
The present invention relates to a process for the preparation of phenethyl tertiary amine derivatives by hydrogenation of phenylacetonitriles. More particularly, the present invention relates to a one pot two step process for the preparation of phenethyl tertiary amine derivatives.
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-
Page/Page column 8
(2009/07/17)
-
- PROCESS FOR THE PREPARATION OF CYCLOHEXANOL DERIVATIVES
-
The present invention relates to a process for the preparation of cyclohexanol derivatives of the general formula (I), wherein R stands for a hydrogen atom or a methyl group, in a one-step process from a cyano compound of the general formula (II).
- -
-
Page/Page column 27-29
(2009/12/27)
-
- In situ or one-pot hydrogenation and reductive amination process
-
An in situ or one-pot process for the preparation of the compounds of formula (I) uses a compound of general formula (I): and includes: a) the hydrogenation of a nitrile group of the compound of general formula (II): in which R1 to R4 are especially H or alkyl and n varies from 0 to 4, in the presence of a hydrogenation catalyst, a methylating agent and an organic acid as solvent, and at a temperature Ta below the initiation temperature of a reductive amination reaction, to give a primary amine from the nitrile group; and b) the reductive amination of the primary amine in the presence of hydrogen, at a temperature Tb above Ta, to give the dimethylated amine of general formula (I) by activation of the methylating age.
- -
-
Page/Page column 3
(2008/12/05)
-
- SOLID FORMS COMPRISING (-) O-DESMETHYLVENLAFAXINE AND USES THEREOF
-
Solid forms comprising a compound useful in the treatment, prevention and management of various conditions and diseases are provided herein. In particular, the invention provides solid forms comprising (-)-O-desmethylvenlafaxine, including salts thereof, having utility for the treatment, prevention and management of conditions and disorders including, but not limited to, affective disorders such as depression, bipolar and manic disorders, attention deficit disorder, attention deficit disorder with hyperactivity, Parkinson's disease, epilepsy, cerebral function disorders, obesity and weight gain, incontinence, dementia and related disorders.
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Page/Page column 63
(2008/12/08)
-
- IMPROVED PROCESS FOR THE PREPARATION OF PHENETHYLAMINE DERIVATIVES
-
The present invention relates to an improved process for the preparation of essentially pure Venlafaxine Hydrochloride. Particularly, the process for the preparation of Venlafaxine Hydrochloride comprises the following steps: i) Preparation of l-[Cyano-l- (4-methoxyphenyl) methyl] cyclohexanol, ii) Preparation of crude Venlafaxine Hydrochloride by reduction of l-[Cyano-l-(4-methoxyphenyl) methyl] cyclohexanol with Alkali metal borohydride and Lewis acid and subsequent conversion to Venalfaxine hydrochloride with formic acid and paraformaldehyde and finally iii) Purification of crude Venlafaxine Hydrochloride.
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-
Page/Page column 7-9
(2008/12/07)
-
- Synthesis of Venlafaxine from azadiene via a Hetero-Diels-Alder approach: New microwave-assisted transketalization and hydroxymethylation reactions
-
Hetero-Diels-Alder (HDA) methodology has been applied to the synthesis of Venlafaxine taking advantage of a novel MW-assisted transketalization and hydroxymethylation reaction.
- Panunzio, Mauro,Bandini, Elisa,D'Aurizio, Antonio,Xia, Zhining,Mu, Xiaojing
-
p. 1753 - 1756
(2008/12/22)
-
- AN IMPROVED PROCESS FOR THE PREPARATION OF VENLAFAXINE AND ITS ANALOGS
-
A novel single step process for the synthesis of venlafaxine of formula I and N-desmethylvenlafaxine of formula II from 2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)acetonitrile [cyano-intermediate] of formula V V comprising reacting 2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)acetonitrile with an alkylamine and/or its salt in a solvent in the presence of a transition metal catalyst, under hydrogen atmosphere.
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-
Page/Page column 15-16
(2008/12/05)
-
- A NOVEL PROCESS FOR PREPARATION OF VENLAFAXINE HYDROCHLORIDE AND ITS INTERMEDIATES
-
A process for the preparation of 1-cyano-[(4-methoxyphenyl)methyl] cyclohexanol by reacting cyclohexanone with the carbanion of 4-methoxyphenyl acetonitrile in the presence of polyethylene glycol-400 (PEG-400) or Aliquate-336, as a phase transfer catalyst (PTC). The present invention also relates to an novel process for the preparation of 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol, using borane-dimethyl sulphide complex (BDMS) or AlCl3-NaBH4, in refluxing tetrahydrofuran. 1-[2-Amino-1-(4-methoxyphenyl)ethyl]cyclohexanol thus obtained was subjected to N,N-dimethylation using formic acid-formaldehyde in boiling 1,4-dioxane: water mixture to obtain 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl] cyclohexanol in high purity, which was treated with isopropanol saturated with HCl gas to get venlafaxine hydrochloride in high purity and high yield.
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-
Page/Page column 8-9
(2008/06/13)
-
- Process for selective synthesis of enantiomers of substituted 1-(2-amino-1-phenyl-ethyl)-cyclohexanols
-
A process for the enantioselective synthesis of an (S)— or (R)-1-[2-dimethylamino)-1-(methoxyphenyl)ethyl]cyclohexanol and analogues or salt thereof are described. The method involves the steps of (a) reacting an (S) or (R) 4-benzyloxazolidinone with a mixed anhydride of a methyoxyphenylacetic acid under conditions which form a oxazolidinone, (4S)— or (4R)-4-benzyl-3-[methyoxyphenyl]acetyl]-oxazolidin-2-one, (b) treating the (4S)— or (4R)-4-benzyl-3-[(methoxyphenyl)acetyl]-1,3-oxazolidin-2-one with an aprotic amine base and titanium chloride in a chlorinated solvent under conditions which permit formation of the corresponding anion, (c) mixing the corresponding anion with titanium chloride and cylcohexanone under conditions which permit an aldol reaction to form the corresponding (4S)— or (4R)-4-benzyl-3-[(2R)-2-(1-hydroxycyclohexyl)-2-(methoxyphenyl)acetyl]-1,3-oxazolidin-2-one, (d) hydrolyzing the (4S)— or (4R)-4-benzyl-3-[(2R)-2-(1-hydroxycyclohexyl)-2-(methoxyphenyl)acetyl]-1,3-oxazolidin-2-one to form a chiral acid (2S or 2R)-(1-hydroxycyclohexyl)-methoxyphenyl)acetic acid, (e) coupling the chiral phenylacid to a secondary amine to form an amide, and (f) reducing the amide to form an (S) or (R) 1[2-dimethylamino)-1-(methoxyphenyl)ethyl]cyclohexanol or a salt thereof.
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Page/Page column 8; 9
(2008/06/13)
-
- PROCESS FOR THE PREPARATION OF HIGHLY PURE 1-[2-DIMETHYLAMINO-(4-METHOXYPHENYL) ETHYL]CYCLOHEXANOL HYDROCHLORIDE
-
The invention encompasses processes for the preparation of highly pure venlafaxine hydrochloride, l-[2-dimethylamino-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride as well as intermediates thereof.
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Page/Page column 21; 22
(2010/11/27)
-
- AN IMPROVED PROCESS FOR THE PREPARATION OF PURE VENLAFAXINE
-
The present invention relates to pure Venlafaxine or salt thereof and a process for preparing highly pure Venlafaxine of structural Formula (I), Formula (I) from N, N-didesmethyl venlafaxine or salt thereof of formula (III).
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-
Page/Page column 9-10; 11-12
(2008/06/13)
-
- Practical synthesis of (±)-venlafaxine
-
A practical total synthesis of antidepressant (±)-venlafaxine is disclosed. Copyright Taylor & Francis Group, LLC.
- Chavan, Subhash P.,Khobragade, Dushant A.,Thakkar, Mahesh,Kalkote, Uttam R.
-
p. 3901 - 3906
(2008/03/13)
-
- Enantioselective synthesis of β-amino esters and its application to the synthesis of the enantiomers of the antidepressant Venlafaxine
-
β-Amino esters are readily formed from the rhodium(ii) prolinate-catalyzed intermolecular C-H insertion between methyl aryldiazoacetates and a bis-silyl protected methylamine. The Royal Society of Chemistry 2006.
- Davies, Huw M. L.,Ni, Aiwu
-
p. 3110 - 3112
(2008/09/20)
-
- PROCESSES FOR PREPARING VENLAFAXINE AND VENLAFAXINE HYDROCHLORIDE OF FORM I
-
A process for preparing venlafaxine in a high yield as well as processes for producing venlafaxine hydrochloride of form I having a very high polymorphic purity are described.
- -
-
Page/Page column 14
(2008/06/13)
-
- Simple and an efficient method for the synthesis of 1-[2-dimethylamino-1- (4-methoxy-phenyl)-ethyl]-cyclohexanol hydrochloride: (±) venlafaxine racemic mixtures
-
A novel synthetic method was developed for the synthesis of venlafaxine using inexpensive reagents. An improvement in the method, in the yield was achieved for the conversion of the venlafaxine. This is an improved version, simple and efficient method for the large-scale synthesis of venlafaxine.
- Basappa,Kavitha,Rangappa
-
p. 3279 - 3281
(2007/10/03)
-
- Crystalline venlafaxine base and novel polymorphs of venlafaxine hydrochloride, processes for preparing thereof
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The present invention relates to novel essentially pure venlafaxine and the process of preparation thereof. The present invention also relates to novel solvate forms of venlafaxine hydrochloride and the process of preparation thereof. Furthermore, the present invention provides a novel process for preparing venlafaxine hydrochloride from venlafaxine; the process comprises the steps of: i) preparing a mixture of venlafaxine with acetone; and ii) exposing the mixture in gaseous hydrochloric acid.
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- An efficient and green protocol for the preparation of cycloalkanols: A practical synthesis of venlafaxine
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The condensation of arylacetonitriles with cyclic ketones using aqueous NaOH or KOH under phase transfer catalysis gives almost quantitative yields of cycloalkanols. This protocol is utilized for a practical synthesis of the antidepression drug, venlafaxine 1.
- Chavan, Subhash P.,Khobragade, Dushant A.,Kamat, Subhash K.,Sivadasan, Latha,Balakrishnan, Kamalam,Ravindranathan,Gurjar, Mukund K.,Kalkote, Uttam R.
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p. 7291 - 7295
(2007/10/03)
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- Derivatives of venlafaxine and methods of preparing and using the same
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Methods of preparing, and compositions comprising, derivatives of venlafaxine are disclosed. Also disclosed are methods of treating and preventing diseases and disorders including, but not limited to, affective disorders such as depression, bipolar and manic disorders, attention deficit disorder, attention deficit disorder with hyperactivity, Parkinson's disease, epilepsy, cerebral function disorders, obesity and weight gain, incontinence, dementia and related disorders.
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- Novel intermediate and processes for its preparation and conversion into a pharmacologically-active agent
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Processes for the preparation of Venlafaxine (IX) via the novel epoxy-nitrile intermediate (I), which when subjected to hydrogenation forms compound (X), and may subsequently be reduced to yield the desired product (IX). The epoxy-nitrile intermediate (I) itself may be synthesised via various alternative reaction strategies, from a range of starting materials. E.g. 4-methoxy-benzaldehyde (VI), upon treatment with cyclohexyl magnesium bromide yields compound (V). This in turn may be oxidised to yield compound (III), which forms compound (II) on treatment with an (x-keto-halogenation agent. Cyanation of compound (II), then yields the desired epoxy nitrile intermediate (I), from which Venlafaxine (IX) may be synthesised.
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- Crystalline venlafaxine base and novel polymorphs of venlafaxine hydrochlorid, processes for preparing thereof
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The present invention relates to novel essentially pure venlafaxine and the process of preparation thereof. The present invention also relates to novel solvate forms of venlafaxine hydrochloride and the process of preparation thereof. Furthermore, the present invention provides a novel process for preparing venlafaxine hydrochloride from venlafaxine; the process comprises the steps of: I) preparing a mixture of venlafaxine with acetone; and ii) exposing the mixture in gaseous hydrochloric acid.
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- Derivatives of (?)-venlafaxine and methods of preparing and using the same
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Methods of preparing, and compositions comprising, derivatives of (?)-venlafaxine are disclosed. Also disclosed are methods of treating and preventing diseases and disorders including, but not limited to, affective disorders such as depression, bipolar and manic disorders, attention deficit disorder, attention deficit disorder with hyperactivity, Parkinson's disease, epilepsy, cerebral function disorders, obesity and weight gain, incontinence, dementia and related disorders.
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- One pot process for the preparation of 1-[2-dimethylamino-(4-methoxyphenyl)-ethyl]cyclohexanol
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A process for the preparation of 2-[dimethylamino-(4-methoxyphenyl)ethyl]-cyclohexanol of formula 1 by reducing 1-[cyano(4-methoxyphenyl)-methyl]cyclohexanol of formula 2 with a formylating agent in a protic solvent in the presence of a catalyst, removing the catalyst by filtration, isolating and purifying the compound of formula 1 is disclosed.
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Page column 3-4
(2008/06/13)
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