Synthesis method for improved cinepazide maleate

A technology of cinepazide maleate and a synthesis method, which is applied in the synthesis field of cinepazide maleate, can solve the problems of wasting time and energy, cumbersome operation, limited production scale and the like, and achieves avoiding steam distillation and The effect of vacuum distillation and simplified process conditions

Inactive Publication Date: 2009-09-16
SHANGHAI NEAO BIO PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the operation of this repeated vacuum distillation is more cumbersome, wastes time and energy, and the production scale is limited
The final yield exceeds the theoretical yield, and there are obviously residual piperazine and inorganic salts that cannot be removed, which will inevitably affect the yield and product purity in the next step

Method used

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  • Synthesis method for improved cinepazide maleate
  • Synthesis method for improved cinepazide maleate
  • Synthesis method for improved cinepazide maleate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Step 1: Preparation of Chloroacetylpyrrolidine

[0034]

[0035] Add 40g of pyrrolidine and 200ml of dichloromethane into a 500ml three-necked flask, cool down to -5°C, and start to drop a total of 250ml of dichloromethane solution dissolved in 63.5g of chloroacetyl chloride and 56.7g of triethylamine. Keep the temperature around 0°C for 2-3 hours to finish dripping. Stir at room temperature for 2 hours, TLC detects that the reaction is complete, stop stirring, filter and wash the filter cake to collect the filtrate, wash the filtrate twice with water, then wash twice with dilute HCl, dry and concentrate the organic phase to obtain chloroacetylpyrrolidine as yellow needle-like crystals 59.5 g, yield: 71.7%.

[0036] Step 2: Preparation of 1-[(1-tetrahydropyrrolecarbonyl)methyl]-4-tert-butoxycarbonylpiperazine

[0037]

[0038] Add 59.5g of chloroacetylpyrrolidine, 820ml of acetone, 78.4g of mono-tert-butoxycarbonylpiperazine, 66.85g of potassium carbonate, and 7...

Embodiment 2

[0052] The solvent in step 2 of the synthetic method is selected as ethanol, the solvent in step 5 is selected as chloroform, the alkali is selected as sodium hydroxide, and the rest are the same as in Example 1, and the yield is similar to that of Example 1.

Embodiment 3

[0054] The solvent in step 2 of the synthetic method is selected as chloroform, the solvent in step 5 is selected as N,N-dimethylformamide, the base is selected as sodium bicarbonate, and the rest are the same as in Example 1, and the yield is similar to that of Example 1.

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Abstract

The invention discloses a synthesis method for improved cinepazide maleate. The synthesis method comprises the following steps: step one: preparing chloracetyl tetrohydropyrrole; step two: preparing 1-[(1-tetrahydropyrrylcarbonyl) methyl]-4-tertbutoxylcarboxypiperazidine; step three: preparing 1-[(1-tetrahydropyrrylcarbonyl) methyl]-piperazidine hydrochloride; step four: preparing 3, 4, 5-trimethoxylcinnamoyl chloride; step five: preparing 1-[(1-tetrahydropyrrylcarbonyl) methyl]-4-(3, 4, 5-trimethoxylcinnamoyl)-piperazidine; step six: preparing 1-[(1-tetrahydropyrrylcarbonyl) methyl]-4-(3, 4, 5-trimethoxylcinnamoyl)-piperazidine maleate. The synthesis route of the environment-friendly cinepazide maleate is economic and practical, green, simplifies operation, saves energy, and generates little waste.

Description

technical field [0001] The invention relates to an improved synthetic method of cinepazide maleate. Background technique [0002] Cinepazide maleate (Cinepazide, 1) chemical name is 1-[(1-tetrahydropyrrolecarbonyl)methyl]-4-(3,4,5-trimethoxycinnamoyl)piperazine maleic butene The diacid salt, a calcium channel blocker, blocks the Ca + Transmembrane into vascular smooth muscle cells to cause smooth muscle relaxation, dilate blood vessels, relieve vasospasm, decrease vascular resistance, increase brain and heart blood flow; enhance the effect of adenosine and cyclic adenosine monophosphate; improve the flexibility and deformation of red blood cells through capillary The capacity of blood vessels, improve microcirculation; reduce blood viscosity, have a protective effect on ischemic organs, etc. Its chemical formula is as shown in (1): [0003] [0004] U.S. Patent (US3634411, patent name: cinnamoyl piperazine; inventor: C. Franc) uses 3,4,5-trimethoxycinnamoyl chloride (I...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/185A61P9/08A61P9/10
Inventor 刘学军雷厉军叶皓刘振德冯冕钱晓庆
Owner SHANGHAI NEAO BIO PHARMA
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