- Synthetic method of venlafaxine hydrochloride intermediate
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The invention provides a synthetic method of a venlafaxine hydrochloride intermediate, the venlafaxine hydrochloride intermediate is a compound 1-[2-amino-1-(4-methoxyphenyl) ethyl] cyclohexanol as shown in a formula I. The method comprises the following steps: carrying out hydrogenation catalytic reaction on a compound 1-cyano-(4-methoxyphenyl) methyl cyclohexanol as shown in a formula II as a raw material; and carrying out hydrogenation catalytic reaction by adopting a copper-nickel catalyst to obtain the compound as shown in the formula I. The venlafaxine hydrochloride produced by the method can effectively control the generation of impurities, and the yield and the purity of the compound shown in the formula I are improved.
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Paragraph 0023-0024; 0026; 0028; 0030; 0032; 0034
(2021/06/02)
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- Method for industrially producing venlafaxine hydrochloride
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The invention discloses a method for industrially producing venlafaxine hydrochloride, and relates to the technical field of drug organic synthesis. The method has the advantages of easily available raw materials of the whole synthetic route, mild reaction conditions, simple and convenient operation, high yield, environment friendliness and good repeatability of the preparation method, and can be used for preparing venlafaxine hydrochloride with high yield and high purity.
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- A method for preparing venlafaxine hydrochloride (by machine translation)
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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)
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Paragraph 0036; 0038; 0039; 0041; 0042; 0044
(2019/04/10)
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- A method for the preparation of venlafaxine hydrochloride (by machine translation)
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The invention discloses a method for the preparation of venlafaxine hydrochloride. The method is provided with the screen of the Raney nickel catalyst in the micro-reactor, at a temperature of 20 - 40 °C lower, compound I with the hydrogen reaction to obtain compound II; compound II by adding sulfuric acid to form the salt to obtain the target product 1 - [2 - amino - 1 - (4 - methoxyphenyl) ethyl] cyclohexanol sulfate (compound III). The present invention provides a micro-reactor on the basis of the Raney nickel sieve catalyst of the creativity of the card in the pipe joint, the catalytic effect is enhanced, and the catalyst can be recycled, at the same time avoid the catalyst mixed in the feed liquid to the micro-reactor slurry pump damage and to avoid reaction of the pipeline blockage. (by machine translation)
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Paragraph 0041-0043
(2017/07/19)
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- A 1 - [2-amino-1 - (4-methoxyphenyl) ethyl] cyclohexanol of the sulphate preparation method
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The invention discloses a preparation method of 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol sulfate. The method comprises the following steps: dissolving 1-cyano-[(4-methoxyphenyl)methyl]cyclohexanol in an organic solvent, and adding a Co-NiO dual catalyst at normal temperature; replacing air in the reactor with hydrogen gas, and reacting for 2-4 hours while controlling the pressure at 0.1-0.5 MPa and the temperature at 80-140 DEG C; after the reaction finishes, cooling the reaction solution to room temperature, filtering, and dropwisely adding concentrated hydrochloric acid into the filtrate; and after finishing the dropwise addition, cooling to 0-10 DEG C, keeping the temperature to crystallize, carrying out vacuum filtration and drying to obtain the 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol sulfate. By adopting the dual catalyst Co-NiO with high catalytic activity, the method shortens the reaction time, enhances the product yield, and has the advantage of simple after-treatment steps; and thus, the technique is easier for industrial production.
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Paragraph 0031-0032
(2016/10/09)
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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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Paragraph 0085
(2015/11/23)
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- An improved and impurity-free large-scale synthesis of venlafaxine hydrochloride
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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
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experimental part
p. 1392 - 1395
(2012/01/13)
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- PROCESS FOR THE PREPARATION OF PHENETHYLAMINE DERIVATIVES
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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 1-[Cyano-1-(4-methoxyphenyl)methyl]cyclohexanol, ii) Preparation of crude Venlafaxine Hydrochloride by reduction of 1-[Cyano-1-(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 4-5
(2010/04/30)
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- A PROCESS FOR THE PREPARATION OF VENLAFAXINE HYDROCHLORIDE
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The present invention relates to a process for the preparation of Venlafaxine Hydrochloride comprising steps of i) treating 4-methoxyphenyl acetonitrile with cyclohexanone in presence of alkali hydroxide and super base to get 1-[cyano (4-methoxyphenyl) methyl] cyclohexanol and ii) reducing 1-[cyano (4-methoxyphenyl) methyl] cyclohexanol in presence of catalyst, activator and alcoholic ammonia under hydrogen pressure.
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Page/Page column 12
(2010/05/13)
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- Preparation of phenethyl tertiary amine derivatives
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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 9
(2009/07/17)
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- AN IMPROVED PROCESS FOR THE PREPARATION OF VENLAFAXINE AND ITS ANALOGS
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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)
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- IMPROVED PROCESS FOR THE PREPARATION OF PHENETHYLAMINE DERIVATIVES
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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)
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- SOLID FORMS COMPRISING (-) O-DESMETHYLVENLAFAXINE AND USES THEREOF
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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)
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- PROCESS FOR THE PREPARATION OF HIGHLY PURE 1-[2-DIMETHYLAMINO-(4-METHOXYPHENYL) ETHYL]CYCLOHEXANOL HYDROCHLORIDE
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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 16; 17
(2010/11/27)
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- A PROCESS FOR THE PREPARATION OF VENLAFAXINE HYDROCHLORIDE
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A process for preparing venlafaxine hydrochloride and also a process for preparing l-[2-amino- l-(4-methoxy phenyl)ethyl]cyclohexanol hydrochloride, an intermediate of venlafaxine hydrochloride are disclosed. p-Methoxy phenyl acetonitrile is condensed with cyclohexanone in the presence of a base selected from alkali metal alkoxides and solvent selected from C4 alcohol at - 10 to - 5° C to obtain l-[cyano-l-(p-methoxy phenyl)m ethyl] cyclohexanol which is directly converted it into the l-[2-amino-l-(4-methoxy phenyl)ethyl] cyclohexanol without being isolated. The molar ratio of base to p-methoxy phenyl acetonitrile or cyclohexanone used is 0.1 to 0.4:1. The l-[2-amino-l-(4-methoxy phenyl)ethyl] cyclohexanol is converted its hydrochloride salt and subsequently formylated to venlafaxine base. The venlafaxine base is further converted into its salt namely venlafaxine hydrochloride. Both venlafaxine hydrochloride and l-[2-amino-l-(4-methoxy ρhenyl)ethyl] cyclohexanol hydrochloride are obtained in high yield with high purity.
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Page/Page column 12-15
(2008/06/13)
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- AN IMPROVED PROCESS FOR THE PREPARATION OF PURE VENLAFAXINE
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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)
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- Process for the preparation of phenethylamine derivatives
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The present invention relates to a process of preparing venlafaxine and derivatives thereof comprising reducing the corresponding β-hydroxynitriles using a reducing borohydride agent selected from tetraalkylammonium borohydride and aralkyltrialkylammonium borohydride. According to the present process, said β-hydroxynitrile can be prepared by condensating a phenylacetonitrile and cyclohexanone using a phase transfer catalyst and a base at a temperature of between 10-25 °C. Advantageously, in the present method, the use of hazardous catalysts and reducing agents is avoided and unexpectedly low amounts of reducing borohydride agent can be used.
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Page/Page column 6
(2008/06/13)
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- A PROCESS FOR THE MANUFACTURE OF VENLAFAXINE AND INTERMEDIATES THEREOF
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The present invention provides an improved process for the preparation of Venlafaxine and the intermediates thereof. The present invention provides a process for preparing compound of formula (IV), an intermediate for preparing Venlafaxine by hydrogenating a compound of formula (III): in the presence of toluene, water, and Raney nickel as catalyst with the process yield of 66% formula (IV) with 99% HPLC purity. The compound of formula (III) is prepared by drop wise addition of p-methoxyphenyl acetonitrile as a solution in tetrahydrofuran to the solution of butyl lithium in hexane the said process yields 89% of compound of formula (III) with 99.8% purity.
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Page/Page column 8-9; 13-14
(2010/10/20)
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- PROCESSES FOR PREPARING VENLAFAXINE AND VENLAFAXINE HYDROCHLORIDE OF FORM I
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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.
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Page/Page column 14
(2008/06/13)
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- PROCESS FOR THE PREPARATION OF ANTI-DEPRESSANT COMPOUND
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A process for the preparation of anti-depressant, compound of formula (I) or its pharmaceutically acceptable salts said process comprising reducing compound of formula (IIa) (wherein R is CONMe2) with sodium bis(2-methoxyethoxy) aluminium hydride followed by optional salt formation.
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Page/Page column 10
(2010/02/12)
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- Process for the preparation of phenethylamine derivative, an intermediate of Venlafaxine hydrochloride
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The present invention relates to an improved process for the preparation of phenethylamine derivatives or salts by hydrogenation of phenylacetonitriles in the presence of heterogeneous palladium on carbon catalyst.
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Page/Page column 3-4
(2010/02/10)
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- 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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- Crystalline forms of venlafaxine hydrochloride
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Crystalline forms of Venlafaxine hydrochloride were found, referred to hereinafter as polymorphic Forms A, B and D. Furthermore, the present invention is directed to processes for the preparation of these crystalline forms and pharmaceutical compositions comprising the crystalline forms.
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- Novel crystalline polymorph of venlafaxine hydrochloride and methods for the preparation thereof
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This invention relates to a highly thermally stable novel anhydrous crystalline polymorphic form of venlafaxine hydrochloride, methods for the preparation thereof, and its use.
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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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