Preparation method of dapoxetine hydrochloride racemate

A technology of cetine racemate and hydrochloric acid, applied in the field of preparation of dapoxetine hydrochloride racemate, can solve the problems of high cost, complicated operation, long steps and the like, and achieve the effects of convenient post-processing and high yield

Inactive Publication Date: 2020-09-11
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented process involves reacting naphtalenes with chloroethanol or ethyleneglyammonium bromochloromyclobutane under specific conditions to produce certain compounds called dapsone that can be used medicinally due to their ability to bind specifically to DNA molecules. These processes are efficient and easy to use at large scales.

Problems solved by technology

This patented describes different types of chemical structures called naproxenone drugs like it: These include both enantiomers with specific properties and pharmacoactive effects on sexual behavior. Napropoxyfonate sodium also known by their name is one example used in medicine. However, there have been reports about side effects caused when these medicines were taken over time from animals exposed during animal testing procedures.

Method used

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  • Preparation method of dapoxetine hydrochloride racemate
  • Preparation method of dapoxetine hydrochloride racemate
  • Preparation method of dapoxetine hydrochloride racemate

Examples

Experimental program
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Embodiment 1

[0033] Synthesis of N,N-dimethylamino-3-(naphthyl-1-oxyl)-1-phenylpropan-1-amine hydrochloride (I)

[0034] Synthesis of 1-bromo-4-(3-bromo-3-phenylpropoxy)naphthalene(III-1)

[0035] Compound 1-(3-phenylpropoxy)naphthalene (II) (26.24g, 0.10mol) was dissolved in carbon tetrachloride (250mL), and benzoyl peroxide (0.25g) and NBS (35.6g , 0.20mol), under the light of tungsten light, slowly heated to reflux within 1 hour, and kept reflux reaction for 4 hours, after the TLC detection reaction was complete, the mixture was cooled, the insolubles were removed by suction filtration, and the filtrate was concentrated under reduced pressure to obtain 41.5 g of reddish-brown oil, yield 98.7%, was directly put into the next reaction without purification.

[0036] Synthesis of 3-((4-bromonaphthalen-1-yl)oxy)-N,N-dimethyl-1-phenyl-propan-1-amine (IV-1)

[0037] Dissolve compound III-1 (41.5g, 98.78mmol) in 280ml of acetone, add 33% dimethylamine solution (33.7g, 246.6mmol), stir for 1 h...

Embodiment 2

[0043] Synthesis of 1-chloro-4-(3-chloro-3-phenylpropoxy)naphthalene(III-2)

[0044] Compound 1-(3-phenylpropoxy)naphthalene (II) (26.24g, 0.10mol) was dissolved in carbon tetrachloride (250mL), and benzoyl peroxide (0.25g) and NCS (29.4g , 0.22mol), under the light of tungsten light, slowly heated to reflux within 1 hour, and kept the reflux reaction for about 4 hours. After the TLC detection reaction was complete, the mixture was cooled, the insolubles were removed by suction filtration, and the filtrate was concentrated under reduced pressure. 30.8 g of reddish-brown oil was obtained with a yield of 93.0%, which was directly put into the next reaction without purification.

[0045] Synthesis of 3-((4-bromonaphthalen-1-yl)oxy)-N,N-dimethyl-1-phenyl-propan-1-amine (IV-2)

[0046] Dissolve compound III-2 (17.0g, 51.3mmol) in 120ml of acetone, add 33% dimethylamine solution (21.0g, 153.7mmol), stir for 1 hour under ice bath, and then reflux for about 5 hours under slight press...

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Abstract

The invention discloses a preparation method of a dapoxetine hydrochloride racemate, which comprises the following steps: by using 1-(3-phenylpropoxy) naphthalene as a raw material, carrying out halogenation, amination, hydrogenation dehalogenation and the like to obtain a dapoxetine hydrochloride racemate (V); the method disclosed by the invention is high in yield, convenient in post-treatment and more suitable for industrial production.

Description

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Claims

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Application Information

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Owner CHINA PHARM UNIV
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