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Preparation method of dapoxetine N-oxide

A technology of urea hydrogen peroxide and naphthyloxy, which is used in the fields of medicine and chemical industry, and can solve the problems of N-oxidation-dapoxetine synthesis and methods that have not been reported.

Inactive Publication Date: 2016-06-08
CHONGQING KANGLE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0016] The synthesis and method of N-oxidation-dapoxetine have not been reported

Method used

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  • Preparation method of dapoxetine N-oxide
  • Preparation method of dapoxetine N-oxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1 Preparation of N-oxidation-Dapoxetine

[0039] Add 50ml of dichloromethane and 10.0g of (S)-N,N-dimethyl-(α)-[2-(1-naphthyloxy)ethyl]benzylamine to the reaction flask, stir and cool to -5°C , Slowly add a dichloromethane solution of urea hydrogen peroxide (6.2g) dropwise, keeping the internal temperature <-5°C, and TLC detects the end of the reaction. After the reaction is complete, add sodium bicarbonate aqueous solution, stir and separate the liquids. The organic phase was washed once with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness under reduced pressure to obtain a brown residue, which was purified by column chromatography and concentrated under reduced pressure to dryness to obtain a brown solid N-oxide-dapoxetine 2.2g, the molar yield is 20.91%.

[0040] According to the HPLC detection conditions of related substances under the item of Dapoxetine raw materials, the detection spectrum of N-oxid...

Embodiment 2

[0041] Example 2 Preparation of N-oxidation-Dapoxetine

[0042] Add 50ml of dichloromethane and 10.0g of (S)-N,N-dimethyl-(α)-[2-(1-naphthyloxy)ethyl]benzylamine to the reaction flask, stir and cool to -5°C , Slowly add a dichloromethane solution of urea hydrogen peroxide (9.3g) dropwise, keep the internal temperature <-5°C, and detect the end of the reaction by TLC. After the reaction is complete, add sodium bicarbonate aqueous solution, stir and separate the liquids. The organic phase was washed once with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness under reduced pressure to obtain a brown residue, which was purified by column chromatography and concentrated under reduced pressure to dryness to obtain a brown solid N-oxide-dapoxetine 2.6g, the molar yield is 24.71%.

Embodiment 3

[0043] Example 3 Preparation of N-oxidation-Dapoxetine

[0044] Add 50ml of chloroform and 10.0g of (S)-N,N-dimethyl-(α)-[2-(1-naphthyloxy)ethyl]benzylamine to the reaction flask, stir and cool to -5°C , Slowly add a chloroform solution of urea hydrogen peroxide (3.1g) dropwise, keep the internal temperature <-5°C, and detect the end of the reaction by TLC. After the reaction is complete, add sodium bicarbonate aqueous solution, stir and separate the liquids. The organic phase was washed once with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness under reduced pressure to obtain a brown residue, which was purified by column chromatography, and concentrated under reduced pressure to dryness to obtain a brown solid N-oxide-dapoxetine 1.8g, the molar yield is 17.11%.

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Abstract

The invention discloses a preparation method of dapoxetine N-oxide (hereinafter referred to as a dapoxetine nitrogen oxide impurity). The dapoxetine nitrogen oxide impurity is an impurity of an oxidized tertiary amine group of dapoxetine in a preparation process, is one of main impurities of raw materials of dapoxetine and can be used for analyzing and detecting HPLC (high performance liquid chromatography) purity of the raw materials of dapoxetine, so that the quality of the raw materials of dapoxetine is controlled.

Description

Technical field [0001] The invention belongs to the technical field of medicine and chemical industry, and specifically relates to N-oxide-dapoxetine, namely (S)-N,N-dimethyl-3-(naphthyl-1-oxy)-1-phenylpropyl -1- Preparation method of nitrogen oxides. Background technique [0002] Dapoxetine, the chemical name is (S)-N,N-dimethyl-(α)-[2-(1-naphthyloxy)ethyl]benzylamine, it is a selective 5 -Serotonin reuptake inhibitor (SSRI) is currently the only drug developed for male premature ejaculation (PE) and the only drug with PE indication approved by the National Food and Drug Administration (CFDA), which can effectively treat male premature ejaculation and sex disfunction. In February 2009, as a drug (priligy) for the treatment of PE, it was first marketed in Sweden and Finland, and then approved in Australia, Germany, Italy, Mexico, New Zealand, Portugal, South Korea, Spain and other countries. The drug is the first in the world Oral prescription drugs used to treat this indicati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C291/04G01N30/02
CPCC07C291/04G01N30/02G01N2030/027
Inventor 张运辉李发万沈文晖马小平郑雪杨继斌蔡中文
Owner CHONGQING KANGLE PHARMA
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