(S)-3-chloro-N, N-dimethyl-1-phenyl-1-propylamine and method for preparing dapoxetine by using same as intermediate

A technology of dapoxetine hydrochloride and dimethyl, applied in the field of treatment of male premature ejaculation

Inactive Publication Date: 2013-11-20
NANJING HERON PHARMA SCI & TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0024] Although the starting materials in the above preparation methods are different, there are problems such as harsh reaction conditions, low yield, difficult access to raw materials, and cumbersome reaction steps

Method used

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  • (S)-3-chloro-N, N-dimethyl-1-phenyl-1-propylamine and method for preparing dapoxetine by using same as intermediate
  • (S)-3-chloro-N, N-dimethyl-1-phenyl-1-propylamine and method for preparing dapoxetine by using same as intermediate
  • (S)-3-chloro-N, N-dimethyl-1-phenyl-1-propylamine and method for preparing dapoxetine by using same as intermediate

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Embodiment Construction

[0040] Below in conjunction with preferred embodiment, the present invention is further described, but the present invention is by no means limited to following embodiment.

[0041] The (R)-3-chloro-1-phenylpropanol used in the present invention was purchased from ***, and other raw materials were purchased from Sinopharm Group.

[0042] 1. Preparation of (S)-3-chloro-N,N-dimethyl-1-phenyl-1-propanamine (3)

[0043] (R)-3-chloro-1-phenylpropanol 3.07g (18.00mmol), dimethylaminopyridine 0.21g (1.75mmol), triethylamine 3.64g (36.00mmol), add 12ml tetrahydrofuran, stir to dissolve, in At 0°C, add dropwise a mixture of 4.12g (36.00mmol) of methanesulfonyl chloride and 3ml of tetrahydrofuran, the dropwise addition is completed within 10 minutes, and the reaction is 6hr; Remove the solvent under pressure, add an appropriate amount of water, adjust the pH to 12-13 with 20% sodium hydroxide solution, add ethyl acetate to extract 3 times, combine the organic layers, wash with water, w...

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Abstract

The invention discloses a method for preparing a dapoxetine intermediate (S)-3-chloro-N, N-dimethyl-1-phenyl-1-propylamine, and preparation of dapoxetine hydrochloride by using the intermediate through condensation and salification. The preparation of dapoxetine hydrochloride is shortened in reaction steps, reduced in cost, simple in operation and is applicable to industrial production.

Description

[0001] technical field [0002] The invention relates to a method for preparing dapoxetine, and its hydrochloride is clinically used. It is mainly used for the treatment of premature ejaculation in men. Background technique [0003] Dapoxetine, chemical name (+)-S-(N,N-dimethylamino)-3-(naphthyloxy-1-oxyl)-1-phenylpropane, structural formula is as follows: [0004] [0005] Its hydrochloride is a selective serotonin uptake inhibitor and an oral drug for the treatment of premature ejaculation in men. [0006] The preparation of dapoxetine mainly includes the following two types of methods. One type of method uses achiral starting materials to react, and finally uses the means of resolution to separate and obtain dapoxetine; the other type of method starts with chiral substances. The starting materials are subjected to multi-step reactions to obtain the final product. [0007] The method using achiral material as starting material is as follows: [0008] (1) EP288188 u...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/29C07C209/16C07C217/48C07C213/06
Inventor 万琴叶海曹卫魏丹柏丹丹
Owner NANJING HERON PHARMA SCI & TECH CO LTD
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