Synthesis method of cinepazide maleate

A technology for the synthesis of cinepazide maleate and a synthesis method, which is applied in the field of synthesis of cinepazide maleate, can solve the problems of high production cost, low boiling point of ether, high requirements for production conditions and equipment, and achieve Simplify production conditions and process, high product yield, good safety effect

Active Publication Date: 2005-06-29
BEIJING SIHUAN PHARMA +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Ether is known to have a very low boiling point and is very flammable;
[0014] The 3rd, when intermediate (III) is synthesized according to the method of literature (2,3), two vacuum distillations are needed in the process of product extraction and purification, which has higher requirements on production conditions and equipment, which is unfavorable for industrial production;
[0015] Fourth, because piperazine is very easy to crystallize during

Method used

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  • Synthesis method of cinepazide maleate
  • Synthesis method of cinepazide maleate
  • Synthesis method of cinepazide maleate

Examples

Experimental program
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Embodiment 1

[0048] The synthesis of embodiment 1 cinepazide maleate:

[0049] 1) synthesis of chloroacetylpyrrolidine

[0050] Reaction formula:

[0051]

[0052] operate:

[0053] Slowly add 300 g of tetrahydropyrrole into a solution of 230 g of chloroacetyl chloride in 1,400 g of dichloromethane under stirring at 10°C. After the addition, continue to stir at room temperature for 2 hours, heat and recover the dichloromethane, and wash the residue with 300 g of ethyl acetate. Dissolve the ester, add 1400g of petroleum ether at 60-80°C, and cool. Tetrahydropyrrole hydrochloride crystallized out, recovered by filtration, and reused after alkalization. The filtrate was washed with 400ml of saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a colorless liquid, which solidified at room temperature to obtain 492g of chloroacetylpyrrolidine, mp. 40-46°C, yield 80%.

[0054] 2) 1-piperazine acetylpyrrolidine:

[0055] Reaction formula:

[0056] ...

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Abstract

The invention relates to a method to synthesize maleic acid cinepazide. (2) reacts with 3,4,5- cinnamyl chloride, aquiring free alkali of cinepazide, the solvent is chosen from 5, add 6 and acquire the (7), the method for separating (1) is filtration. The invention uses safe solvent in the synthesis of (2), and the method of filtration and 8, making it suitable for industrialized production. The method uses the solvent with low toxicity and good safety, simplized productive condition and course, has high productivity and low cost.

Description

Technical field: [0001] The invention relates to a synthesis method of cinepazide maleate. Background technique: [0002] Cinepazide maleate is a peripheral vasodilator, clinically used for the treatment of cardiovascular and cerebrovascular diseases. Its English name is Cinepazide Maleate, and its chemical name is: trans-{(1-pyrrolidinecarbonyl)methyl}-4-(3,4,5-trimethoxycinnamoyl)-piperazinemaleate. [0003] The chemical structural formula (I) of cinepazide maleate is as follows: [0004] [0005] The synthetic route of cinepazide maleate reported in Patent Document 1 (C.P.Fauran et al: US 3634411) is shown in Synthetic Route 1: with trans-3,4,5-trimethoxycinnamoyl chloride (II) and 1-piperazine acetylpyrrolidine (III) is used as a starting material, anhydrous benzene is used as a solvent, and sodium bicarbonate is used as an acid absorbing agent to carry out condensation reaction to obtain cinepazide, which is then salted with maleic acid. [0006] [0007] ...

Claims

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Application Information

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IPC IPC(8): C07D207/08
Inventor 高建华
Owner BEIJING SIHUAN PHARMA
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