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Preparation method of succinylcholine chloride

A technology of succinylcholine chloride and choline chloride, which is applied in the preparation of organic compounds, chemical instruments and methods, and the preparation of amino hydroxyl compounds, can solve the problems of serious pollution, environmental pollution, and high cost, and achieve high reaction efficiency , no sulfur dioxide pollution, easy to operate

Inactive Publication Date: 2016-01-20
ZHEJIANG ESIGMA BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthesis of the intermediate succinyl chloride requires thionyl chloride chlorination, which produces a large amount of sulfur dioxide gas, which leads to serious environmental pollution.
[0007] The existing method for preparing succinylcholine chloride has problems such as low yield, high cost, serious pollution, etc. Therefore, the preparation method of succinylcholine chloride with high yield and low cost is of great significance for the popularization and application of quick-acting muscle relaxants. Significance

Method used

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  • Preparation method of succinylcholine chloride
  • Preparation method of succinylcholine chloride

Examples

Experimental program
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Effect test

Embodiment 1

[0027] Add 11.81g (0.1mol) of succinic acid, 35.43g of dichloroethane and 0.37g (0.005mol) of DMF into the three-necked flask, and slowly add BTC-C below 10°C 2 h 4 Cl 2 After adding 25ml, heat up to reflux and react for 1 hour. After the reaction is over, cool down to room temperature to obtain a dichloroethane solution of succinyl chloride; add 27.93g (0.2mol) of choline chloride to the above solution, and heat up to reflux for 30min. , Dichloroethane was recovered by distillation under reduced pressure and residual hydrogen chloride gas was removed, 23.62 g of ethanol was added, the pH of the reaction solution was adjusted to 4.5 with pyridine under stirring, cooled to below 10°C to crystallize, filtered, and dried to obtain succinylcholine chloride 31.59 g, the HPLC purity is 99.36%, and the yield is 86.87%.

Embodiment 2

[0029] Add 11.81g (0.1mol) of succinic acid, 23.62g of dichloroethane and 0.37g (0.005mol) of DMF into the three-necked flask, and slowly add BTC-C below 10°C 2 h 4 Cl 2 After adding 26.7ml, heat up to reflux for 1.5 hours. After the reaction is over, cool down to room temperature to obtain a dichloroethane solution of succinyl chloride; add 34.9g (0.25mol) of choline chloride to the above solution, and heat up to reflux to react After 20 minutes, recover dichloroethane and remove residual hydrogen chloride gas by distillation under reduced pressure, add 35.43 g of ethanol, adjust the pH of the reaction solution to 4 with pyridine under stirring, cool to below 10°C to crystallize, filter, and dry to obtain succinylcholine chloride 32.12g, HPLC purity 99.47%, yield 88.43%.

Embodiment 3

[0031] Add 11.81g (0.1mol) of succinic acid, 47.24g of dichloroethane and 0.37g (0.005mol) of DMF into the three-necked flask, and slowly add BTC-C below 10°C 2 h 4 Cl 2 After adding 26ml, heat up to reflux for 2 hours. After the reaction is over, cool down to room temperature to obtain a dichloroethane solution of succinyl chloride; add 41.88g of choline chloride to the above solution, heat up to reflux for 50 minutes, and distill under reduced pressure. Recover dichloroethane and remove residual hydrogen chloride gas, add 47.24g of ethanol, adjust the pH of the reaction solution to 4 with pyridine under stirring, cool to below 10°C to crystallize, filter and dry to obtain 32.31g of succinylcholine chloride, HPLC purity It is 99.48%, and the yield is 88.96%.

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Abstract

The invention provides a preparation method of succinylcholine chloride. The preparation method includes the specific operating steps that succinic acid, dichloroethane and DMF are added to a reaction container, a BTC / C2H4Cl2 solution is slowly added in a dropwise mode at the temperature below 10 DEG C, the temperature is raised after the solution is added for a backflow reaction for 1-2 h, after the reaction is completed, temperature is reduced to room temperature, and a dichloroethane solution of succinyl chloride is obtained; choline chloride is added to the solution, the temperature is raised to the backflow temperature to react for 20-50 min, dichloroethane is recycled and residual hydrogen chloride gas is removed through reduced pressure distillation, ethyl alcohol is added, the PH of reaction liquid is adjusted to 4 to 4.5 through pyridine under stirring, the reaction liquid is crystallized and filtered when cooled below 10 DEG C, and needed succinylcholine chloride is obtained after drying. The BTC / C2H4Cl2 solution is adopted as a reagent of sulfonyl chlorination, the reaction efficiency is high, side reactions are fewer, no sulfur dioxide pollution is generated, the significance of environment-friendly production is achieved, the purity of obtained succinylcholine chloride is more than 99%, the yield is more than 86%, and the preparation method is mild in reaction condition, simple in process, easy to operate and suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of fine chemical industry (drug synthesis), in particular to a preparation method of succinylcholine chloride. Background technique [0002] Choline chloride is white or almost white crystalline powder, odorless, salty, easily soluble in water, slightly soluble in ethanol or chloroform, insoluble in ether. Its molecular formula is C 4 h 34 C 12 N 2 o 6 , the molecular weight is 397.34. Its structural formula is as follows: [0003] [0004] Succinylcholine chloride is a polarized muscle relaxant and a synthetic substitute of tubocurarine. Its muscle relaxation effect is fast; the duration is short; it is easy to control; it is very suitable for use in minor surgical operations and tracheal intubation. [0005] Generally, succinylcholine chloride is obtained by condensation of succinyl chloride and choline chloride. If the reaction is incomplete, impurities such as choline chloride may remain. The United Sta...

Claims

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Application Information

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IPC IPC(8): C07C219/06C07C213/06
Inventor 吴中华张小朋陈贵才徐天华何奇雷闻鸣
Owner ZHEJIANG ESIGMA BIOTECH CO LTD
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