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Method for synthesizing citric acid diphenhydramine

A diphenhydramine citrate and synthesis method technology, applied in chemical instruments and methods, carboxylate preparation, organic compound preparation, etc., can solve the problems of cumbersome and complicated operations, low product yields, etc., and achieve simplified operations steps, simplify the purification steps, and shorten the production cycle

Inactive Publication Date: 2011-11-02
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But above-mentioned two kinds of methods are all loaded down with trivial details and complicated operation, and product yield is lower

Method used

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  • Method for synthesizing citric acid diphenhydramine
  • Method for synthesizing citric acid diphenhydramine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Embodiment 1, the synthesis of bisbenzyl alcohol-beta-chloroethyl ether

[0022] Add 92g of benzhydryl alcohol, 40g of chloroethanol, and 21.8ml of sulfuric acid with a mass fraction of 98% into a three-necked flask (the molar ratio of benzhydryl alcohol, chloroethanol and sulfuric acid is 1:1:0.8), heat up to 70°C and keep the reaction. The reaction process was monitored by thin-layer chromatography. After 6 hours of reaction, the mixture was allowed to stand for stratification, and the oily liquid in the upper layer was collected, washed 3 times with 25% sodium carbonate solution with a mass fraction, and then washed 3 times with hot water at a temperature of 60°C. That is, bisbenzyl alcohol-β-chloroethyl ether was obtained with a yield of 78.5%.

[0023]

Embodiment 2

[0024] Embodiment 2, the synthesis of benzyl alcohol-beta-chloroethyl ether

[0025] Add 92g of benzhydryl alcohol, 52.3g of chloroethanol, and 16.3ml of sulfuric acid with a mass fraction of 98% into a three-necked flask (the molar ratio of benzhydryl alcohol, chloroethanol and sulfuric acid is 1:1.3:0.6), and heat up to 100°C for reaction , monitor the reaction process with thin-layer chromatography, after 4 hours of reaction, let it stand for stratification, collect the oily liquid in the upper layer, wash 3 times with 15% sodium carbonate solution with a mass fraction, and then wash 3 times with hot water at a temperature of 80°C , that is, bisbenzyl alcohol-β-chloroethyl ether was obtained with a yield of 84.3%.

[0026]

Embodiment 3

[0027] Embodiment 3, the synthesis of bisbenzyl alcohol-beta-chloroethyl ether

[0028] Add 92 g of benzhydryl alcohol, 60.4 g of chloroethanol, and 10.9 ml of sulfuric acid with a mass fraction of 98% into a three-necked flask (the molar ratio of benzyl alcohol, chloroethanol and sulfuric acid is 1:1.5:0.4), heat up to 130°C and keep the reaction , monitor the reaction process with thin-layer chromatography, after 3 hours of reaction, let it stand for stratification, collect the oily liquid in the upper layer, wash 3 times with 5% sodium carbonate solution with a mass fraction, and then wash 3 times with hot water at a temperature of 100°C , that is, bisbenzyl alcohol-β-chloroethyl ether was obtained with a yield of 73.6%.

[0029]

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PUM

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Abstract

The invention relates to a method for synthesizing citric acid diphenhydramine by a 'one boiler method'. The method comprises the following steps of: reacting diphenyl methanol-beta-chloroethylether with dimethylamine to generate diphenhydramine hydrochloride; adding sodium hydroxide to treat, so that the diphenhydramine is freed; and directly adding citric acid into the same reactor to perform acid-base reaction to prepare the citric acid diphenhydramine. By the method, an intermediate is not required to be separated and purified, so the operating steps can be simplified, yield of the products can be increased, production cycle can be shortened, and production cost can be reduced; the starting raw material diphenyl methanol-beta-chloroethylether can be obtained from a commercial channel or can be prepared by reacting diphenyl methanol with 2-chlorohydrin in the presence of concentrated sulfuric acid without using a toxic organic solvent, so the subsequent purification step is simplified and safety of personnel operation and products is improved; and a method for synthesizing the diphenyl methanol-beta-chloroethylether is combined with the method for synthesizing the citric acid diphenhydramine, remarkable effects of simplifying the operating steps, increasing the yield of the products and reducing the production cost are achieved.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a method for synthesizing raw materials, in particular to a method for synthesizing diphenhydramine citrate. Background technique [0002] Diphenhydramine citrate (structural formula below) has antihistamine, sedative, local anesthesia, anti-emetic and anti-M-choline-like effects, and is often used clinically for skin and mucous membrane allergies, acute allergic reactions, prevention and treatment of motion sickness and seasickness, and hypnosis And preoperative administration, dental local anesthesia, antitussive, etc., can also be used for anti-parkinsonian paralysis, and can also be combined with other drugs to treat Parkinson's disease and extrapyramidal symptoms. Compared with diphenhydramine hydrochloride, diphenhydramine citrate has enhanced stability, reduced bitterness, reduced irritation, increased fat solubility and easy absorption. [0003] [0004] U.S. Patent ...

Claims

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Application Information

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IPC IPC(8): C07C217/10C07C213/02C07C59/265C07C51/41
Inventor 李逐波陈立刘衍季刘天亮赖翔宇刘晓华向春艳童南南
Owner SOUTHWEST UNIVERSITY
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