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The preparation method of n-(5-methoxy-3-indolethyl)-4-substituted phenylpiperazine-1-acetamide

A technology of indoleethyl and phenylpiperazine, which is applied in the field of preparation of N--4-substituted phenylpiperazine-1-acetamide, can solve problems such as cumbersome operation, high toxicity, and difficult solvent recovery, and achieve The effect of safe and simple process operation, reduced toxicity and stable product quality

Active Publication Date: 2015-10-28
SHANGHAI SHISI CHEM PROD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The technical problem to be solved by this invention is to provide a kind of preparation method of N-(5-methoxyl-3-indolethyl)-4-substituted phenylpiperazine-1-acetamide, to overcome the The use of substituted benzene as a solvent is highly toxic, solvent recovery is difficult, and the operation is cumbersome.

Method used

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  • The preparation method of n-(5-methoxy-3-indolethyl)-4-substituted phenylpiperazine-1-acetamide
  • The preparation method of n-(5-methoxy-3-indolethyl)-4-substituted phenylpiperazine-1-acetamide
  • The preparation method of n-(5-methoxy-3-indolethyl)-4-substituted phenylpiperazine-1-acetamide

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Experimental program
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Effect test

Embodiment 1

[0026] In the reactor with low temperature and constant temperature reaction bath, stirring, thermometer, and reflux condenser, add 100ml ether, 23.7g (0.11mol) N-(4-methylphenyl)piperazine-1-acetic acid methyl ester, 1.4g sodium methoxide, control the reaction temperature 0-5 ℃, stir to obtain N-(4-methylphenyl)piperazine-1-acetic acid methyl ether mixture, add dropwise 20.9g (0.11mol) 5 - 5-methoxytryptamine ethyl ether solution composed of methoxytryptamine and 100ml ether, after reacting at the same temperature for 2 hours, slowly raise the temperature to 30°C, continue the reaction for 4 hours, and post-process the obtained reaction solution.

[0027] Add 10wt% dilute hydrochloric acid to wash until the pH value of the reaction solution is 5.6, wash the reaction solution twice with 20ml and 60ml of saturated sodium chloride solution after liquid separation, separate the liquid, dry with anhydrous sodium sulfate, filter, and recover by distillation under reduced pressure d...

Embodiment 2

[0029] In the reactor with low temperature and constant temperature reaction bath, stirring, thermometer, reflux condenser, add 100ml tetrahydrofuran, 27.6g (0.11mol) ethyl N-(4-chlorophenyl)piperazine-1-acetate, 1.8 g sodium ethoxide, control the temperature of the reactor at 0-10°C, stir to obtain N-(4-chlorophenyl)piperazine-1-ethyl acetate tetrahydrofuran mixture, dropwise add 22.8g (0.12mol) of 5- The 5-methoxytryptamine tetrahydrofuran solution composed of methoxytryptamine and 100ml tetrahydrofuran was controlled at a reaction temperature of 5-10°C for 4 hours, then slowly raised to 30°C, and the reaction was continued for 4 hours, and the obtained reaction solution was post-treated.

[0030] Add 5wt% dilute hydrochloric acid to wash until the pH value of the reaction solution is 5.8, wash the reaction solution twice with 20ml and 60ml saturated sodium chloride solution after liquid separation, separate the liquid, dry with anhydrous sodium sulfate, filter, and recover t...

Embodiment 3

[0032] Add 150ml 2-methyltetrahydrofuran, 24.3g (0.10mol) N-(4-fluorophenyl)piperazine-1-acetic acid respectively Ethyl ester, 2.3g sodium ethoxide, control reaction temperature 5-10 ℃, stir to obtain N-(4-fluorophenyl)piperazine-1-ethyl acetate 2-methyltetrahydrofuran mixed solution, drop in 40 minutes by 28.5 5-methoxytryptamine 2-methyltetrahydrofuran solution composed of g (0.15mol) 5-methoxytryptamine and 100ml 2-methyltetrahydrofuran, reacted at the same temperature for 3 hours, then slowly raised the temperature to 50°C, and continued the reaction for 4 Hours, the resulting reaction solution was post-treated.

[0033]Add 10wt% dilute hydrochloric acid to wash until the pH value of the reaction solution is 5.6, wash the reaction solution twice with 20ml and 60ml saturated sodium chloride solution after liquid separation, separate the liquid, dry with anhydrous sodium sulfate, filter, and recover by distillation under reduced pressure 2-Methyltetrahydrofuran to obtain cr...

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Abstract

The invention discloses a method for preparing N-(5-methoxy-1H-indole-3-ethyl)-4-subtituted phenylpiperazine-1-acetamide, which is implemented by taking an ether reagent as a reaction solvent through the steps of: in the presence of a strong basic catalyst, reacting N-(4-substituted phenyl)piperazine-1-acetate with 5-methoxytryptamine so as to obtain a coarse N-(5-methoxy-1H-indole-3-ethyl)-4-subtituted phenylpiperazine-1-acetamide product; and then, carrying out washing, drying and recrystallization on the obtained coarse N-(5-methoxy-1H-indole-3-ethyl)-4-subtituted phenylpiperazine-1-acetamide product so as to obtain a target product. Through detection, the purity of the prepared N-(5-methoxy-1H-indole-3-ethyl)-4-subtituted phenylpiperazine-1-acetamide is greater than or equal to 97.5%, the yield thereof is greater than or equal to 57%, and the melting point thereof is 148-152 DEG C. By using the method disclosed by the invention, the shortcomings of large toxicity, difficult recovery and cumbersome operation of benzene solvents are overcome, and the potential environmental-friendliness hazards existing in taking pyridine and zinc powder as catalysts are avoided; and the toxicity of raw materials is reduced, the yield is significantly improved, the operation is safe and convenient, and the product quality is stable, therefore, the method is suitable for large-scale industrialized production.

Description

technical field [0001] The invention relates to a preparation method of N-(5-methoxy-3-indolethyl)-4-substituted phenylpiperazine-1-acetamide. Background technique [0002] N-(5-methoxy-3-indolethyl)-4-substituted phenylpiperazine-1-acetamide as an α 1 - Receptor antagonists are effective drugs for the clinical treatment of benign prostatic hyperplasia, the existing α 1 - Receptor antagonists mainly include quinazolines, piperidines, phenylpiperazines and phenethylamines. Studies have shown that most phenylpiperazines have good urinary tissue selectivity and alpha 1 - Receptor subtype selectivity, its structural formula is as follows: [0003] [0004] where R 1 =F, Cl, Br, I, CH 3 , C 2 h 5 , i-C 3 h 7 , n-C 3 h 7 , i-C 4 h 9 , n-C 4 h 9 , OCH 3 , OC 2 h 5 , CF 3 ; 2 =CH 3 , C 2 h 5 , i-C 3 h 7 , n-C 3 h 7 , i-C 4 h 9 , n-C 4 h 9 . [0005] In the prior art, Wu Bin et al [Synthesis and biological activity of N-(5-methoxy-3-indoleethyl)-4-s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/14
Inventor 张传好宋振蒋旭亮詹家荣
Owner SHANGHAI SHISI CHEM PROD
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