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Method for synthesizing cinepazide

A synthesis method and technology of cinnamic acid, applied in the field of medicine and chemical industry, can solve the problems of many by-products, complicated post-processing steps, low yield of reaction products, etc., and achieve the effects of low cost, easy industrial production, and simple post-processing

Active Publication Date: 2011-11-02
JIANGSU SHENLONG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

What this synthetic route adopts is to use trans-3,4,5-trimethoxycinnamic acid to react with 1-[1-(1-pyrrolidinecarbonyl)methyl]piperazine after activation with carboxyl activator to prepare Cinepezil Special, but the carboxyl activator used is a small molecular compound, the activating group is not easy to fall off, the by-products are more, the post-processing steps are cumbersome, and the yield of the reaction product is low

Method used

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  • Method for synthesizing cinepazide
  • Method for synthesizing cinepazide
  • Method for synthesizing cinepazide

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Embodiment 1

[0033] Trans-3,4,5-trimethoxycinnamic acid (40.0g, 0.168mol), 2-chloro-4,6-dimethyl-s-triazine (30.0g, 0.171mol) were stirred and dissolved in 250ml of dichloromethane , slowly add N-methylmorpholine (28.7g, 0.333mol) dropwise under stirring, after 2 hours of heat preservation reaction, filter to obtain cinnamic acid activation product solution; then add 1-[1-(1-pyrrolidinylcarbonyl) Methyl]piperazine (30.0 g, 0.152 mol) was stirred and dissolved in dichloromethane, and the cinnamic acid activator solution was slowly added dropwise under stirring, and the reaction was kept for 5 hours. After the reaction was completed, the reaction solution was washed with 120ml saturated aqueous sodium bicarbonate solution, washed with purified water, and then extracted with dilute hydrochloric acid solution (3mol / L) 100ml*3 times, and the dilute hydrochloric acid layer was adjusted to pH with 20% sodium hydroxide to more than 12, then extract 100ml*3 times with dichloromethane, wash the dich...

Embodiment 2

[0035]Trans-3,4,5-trimethoxycinnamic acid (40.0g, 0.168mol), 2-chloro-4,6-dimethyl-s-triazine (30.0g, 0.171mol) were stirred and dissolved in 250ml of acetone, stirred Slowly add triethylamine (34.0g, 0.334mol) dropwise under heat preservation reaction for 2 hours, filter to obtain cinnamic acid activation product solution; then add 1-[1-(1-pyrrolidinecarbonyl)methyl]piperazine (30.0 g, 0.152 mol) was stirred and dissolved in acetone, and the cinnamic acid activator solution was slowly added dropwise under stirring, and the reaction was kept for 5 hours. After the reaction was completed, the reaction solution was washed with 120ml saturated aqueous sodium bicarbonate solution, washed with purified water, and then extracted with dilute hydrochloric acid solution (3mol / L) 100ml*3 times, and the dilute hydrochloric acid layer was adjusted to pH with 20% sodium hydroxide to more than 12, then extract 100ml*3 times with dichloromethane, wash the dichloromethane layer with 100ml sat...

Embodiment 3

[0037] Trans-3,4,5-trimethoxycinnamic acid (40.0g, 0.168mol), bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride (43.5g, 0.171mol) was stirred and dissolved in 250ml In dichloromethane, diisopropylethylamine (43.05g, 0.333mol) was slowly added dropwise under stirring, and after heat preservation for 2 hours, it was filtered to obtain a cinnamic acid activation product solution; then 1-[1-(1- Pyrrolidinecarbonyl)methyl]piperazine (30.0g, 0.152mol) was stirred and dissolved in dichloromethane, and the cinnamic acid activator solution was slowly added dropwise under stirring, and the reaction was kept for 5 hours. After the reaction was completed, the reaction solution was washed with 120ml saturated aqueous sodium bicarbonate solution, washed with purified water, and then extracted with dilute hydrochloric acid solution (3mol / L) 100ml*3 times, and the dilute hydrochloric acid layer was adjusted to pH with 20% sodium hydroxide to more than 12, then extract 100ml*3 times with dichlorom...

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Abstract

The invention discloses a method for synthesizing cinepazide. The method for synthesizing the cinepazide comprises the step of reacting an activated substance of 3,4,5-trimethoxy cinnamic acid with 1-[1-(1-pyrrolidine carbonyl)methyl]piperazine or salt thereof to obtain the cinepazide. Benzene high-toxicity solvents are not used in the whole reaction process, so the method is environment-friendly and safe in industrial production; the reaction steps are few, so the method is easy to operate; the method is mild in condition, simple in aftertreatment and suitable for industrialized production; special or complex reaction equipment is not required; and the product has high purity. The invention provides a synthetic route of the cinepazide, with high reaction yield and low cost.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, in particular to a kind of cinepazide, that is, trans-1-[(1-pyrrolidinecarbonyl)]methyl]-4-(3,4,5-trimethoxycinnamoyl)piper Synthetic method of oxazine. Background technique [0002] Cinepazide maleate, trans-1-[(1-pyrrolidinecarbonyl)]methyl]-4-(3,4,5-trimethoxycinnamoyl)piperazine maleate , the structural formula is as follows: [0003] [0004] Cinepazide maleate is a cardiovascular drug that can prevent calcium ions from entering vascular smooth muscle cells across the membrane, causing smooth muscle relaxation, dilating blood vessels, relieving vasospasm, reducing vascular resistance, and increasing blood flow in the brain and heart. It is widely used clinically to treat various cardiovascular and cerebrovascular diseases. [0005] [0006] 专利文献(US3634411、ES447859、JP2180876A、CN101508685A、CN1876646A、CN1246310C、CN101260092A、CN 100572378C、CN 101955472A、CN 101531643A、CN 101...

Claims

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Application Information

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IPC IPC(8): C07D295/185
Inventor 胡传良苏晋秦勇金春沈平平周超王莎莎
Owner JIANGSU SHENLONG PHARMA
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