cas 908291-72-5, 3-(1-Naphthalenyloxy)-1-phenyl-1-propanol

Articles about 908291-72-5Total 12 be found

Synthesis method of dapoxetine and dapoxetine hydrochloride
The invention provides a synthesis method of dapoxetine and dapoxetine hydrochloride, and belongs to the technical field of organic synthesis of medicines. The synthesis method of dapoxetine provided by the invention comprises the following steps: 1-naphthol and paraformaldehyde generate 1-naphthol bromomethyl ether under the action of hydrogen bromide, the 1-naphthol bromomethyl ether reacts with magnesium to obtain a 1-naphthol bromomethyl ether Grignard reagent, the 1-naphthol bromomethyl ether Grignard reagent reacts with R-styrene oxide to obtain R-3-(1-naphthyloxy)-1-phenyl propanol, and the R-3-(1-naphthyloxy)-1-phenyl propanol reacts with a bromination reagent to obtain S-1-bromo-1-phenyl-3-(1-naphthyloxy)propane; or the S-1-bromo-1-phenyl-3-(1-naphthyloxy)propane reacts with sulfonyl chloride to obtain S-1-sulfonyloxy-1-phenyl-3-(1-naphthyloxy) propane, or and the S-1-sulfonyloxy-1-phenyl-3-(1-naphthyloxy)propane reacts with sulfonyl chloride to obtain dapoxetine hydrochloride. The synthesis method provided by the invention has the advantages of short synthesis route, high product yield, good product quality, easily available raw materials, low cost and small environmental pollution, and is suitable for industrial production.
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Paragraph 0055; 0088; 0091-0093; 0100; 0103-0105; 0112; ...

(2021/10/02)

Related substances of dapoxetine hydrochloride, preparation method and applications thereof
The invention relates to related substances of dapoxetine hydrochloride, a preparation method and applications thereof, wherein the related substances are (R)-3-((R)-3-(naphthalene-1-oxy)-1-phenylpropoxy)-1-phenylpropyl-1-ol and/or (S)-N,N-dimethyl-3-((R)-3-(naphthalene-1-oxy)-1-phenylpropoxy)-1-phenylpropyl-1-amine and a salt thereof, especially a hydrochloride. According to the invention, by detecting and controlling the related substances provided by the invention in the production and quality inspection of dapoxetine hydrochloride, an intermediate, a bulk drug and a preparations thereof, the drug quality of dapoxetine hydrochloride is further improved, possible side effects are reduced, and the medication safety is improved.
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Paragraph 0127-0129

(2020/04/17)

Synthetic method of dapoxetine
The invention belongs to the technical field of medicines, in particular to a synthetic method of dapoxetine. The synthetic method comprises the following steps: adding 1-naphthol and 1-phenyl-3-chloropropanol into acetone as a solvent at a temperature of
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Paragraph 0039; 0040-0044

(2019/04/04)

Preparation method of dapoxetine hydrochloride
The invention belongs to the technical field of drug preparation and particularly relates to a preparation method of dapoxetine hydrochloride. The method comprises steps as follows: a compound 3 and alkali are dissolved in an organic solvent for a reaction, then, a compound 2 is added, an esterification reaction is performed, and a compound 4 is obtained; the compound 4 is subjected to asymmetric reduction by a chiral reducing agent in an organic solvent, and a compound 5 is obtained; the compound 5 reacts with MsCl, trimethylamine and 4-dimethylamino-pyridine in an organic solvent, dimethylamine hydrochloride is added for a further reaction, a product is added to water, extracted with ethyl acetate and steamed to form an oily substance, cooling, crystallization and suction filtration are performed, dapoxetine free alkali solids are obtained and dissolved in isopropanol, an isopropanol solution of hydrogen chloride is added and crystalized, and dapoxetine hydrochloride is obtained. The chemical purity and the optical purity are high, the quality is stable, operation is simple and convenient, the yield is high, the quality is stable, large-scale production is facilitated, the production cycle is shorter, and the synthesis route is shown in the specification.
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(2018/04/01)

Enantioselective β-hydroxy thioesters formation via decarboxylative aldol reactions of malonic acid half thioesters with aldehydes promoted by chloramphenicol derived sulfonamides
A highly enantioselective synthesis of chiral β-hydroxy thioesters that uses a decarboxylative aldol reaction of malonic acid half thioesters and aldehydes catalyzed by a chloramphenicol base-derived bifunctional organocatalyst is reported. The resulting
Wang, Yafeng,Huang, Guanxin,Hu, Sha,Jin, Kaijun,Wu, Yan,Chen, Fener
p. 5055 - 5062
(2017/07/28)

A hydrochloric acid west reaches anchors the sandbank preparation method (by machine translation)
The invention discloses a method for preparing west reaches anchors the sandbank hydrochloride, including 3 - chlorobenzene propanol, 1 - phenyl - 3 - (1 - naphthoxy) - 1 - propanol, preparation of pure west reaches anchors the sandbank, west reaches anchors the sandbank DTTA salt preparation, preparation of west reaches anchors the sandbank, hydrochloric acid west reaches anchors the sandbank crude preparation and hydrochloric acid west reaches anchors the sandbank preparation of the finished product, the invention, accelerate the speed of production, the saving in material. (by machine translation)
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(2017/08/29)

Chiral preparation method of dapoxetine hydrochloride key intermediate
The invention discloses a chiral preparation method of a dapoxetine hydrochloride key intermediate.According to the preparation method, with 3-chloropropiophenone as a raw material and (+)2-ethylmorphine-B-chlorodiisopinocampherylborane Eap2BCl as a reduc
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(2017/02/09)

Stereoselective synthesis of (S)-dapoxetine: A chiral auxiliary mediated approach
An imidazolidin-2-one chiral auxiliary mediated acetate aldol reaction was explored in the enantioselective synthesis of (S)-dapoxetine (SSRI). The diastereoselective aldol adduct was transformed to highly enantiopure (S)-dapoxetine with overall good yield.
Khatik, Gopal L.,Sharma, Ratnesh,Kumar, Varun,Chouhan, Mangilal,Nair, Vipin A.
p. 5991 - 5993
(2013/10/22)

Corey-itsuno reduction of ketones: A development of safe and inexpensive process for synthesis of some API intermediates
A safe and inexpensive procedure for asymmetric reduction of ketones using in situ prepared N,N-diethylaniline borane (DEANB) and oxazaborolidine catalyst from sodium borohydride, N,N-diethylaniline hydrochloride and (S)-α,α-diphenylprolinol is described. This protocol is demonstrated successfully to manufacture enantiopure dapoxetine at the plant scale.
Mahale, Rajendra D.,Chaskar, Sudhir P.,Patil, Kiran E.,Maikap, Golak C.,Gurjar, Mukund K.
p. 710 - 713
(2012/07/27)

Simple and efficient synthesis of (S)-dapoxetine
A refinement in the synthetic strategy for (S)-dapoxetine 1 is described. The key features of synthetic strategy include (a) a Sharpless asymmetric epoxidation reaction and regioselective reductive ring opening of a 2,3-epoxy alcohol to elaborate the hydroxy-bearing stereogenic center at benzylic position; (b) regioselective functionalization of 1-naphthol and amine functionality through Mitsunobu procedures; and (c) Eschweiler-Clarke reductive methylation condition to access the target molecule.
Sasikumar,Nikalje, Milind D.
p. 3061 - 3067
(2012/08/27)

PROCESS FOR PREPARING DAPOXETINE
This invention relates to a new process for preparation of enantiomerically pure dapoxetine or an acid addition salt thereof i.e. S(+)-N,N-dimethyl-2-[2-(naphthalenyl oxy)ethyl]benzenemethanamine hydrochoride, a potent serotonin re-uptake inhibitor (SSRI), which comprises resolving racemic (±)-dapoxetine i.e. (±)- N,N-dimethyl-2-[2- (naphthalenyloxy)ethyl] benzene methanamine with a chiral acid so as to obtain salt of the chiral acid and (+)-dapoxetine, substantially free from (-)-dapoxetine.
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Page/Page column 8; 10-11

(2010/11/30)