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Method for preparing high-purity cetirizine hydrochloride

A kind of cetirizine hydrochloride, cetirizine technology, applied in the field of medicine and chemical industry, can solve the problems of difficult to guarantee product quality, high price of potassium tert-butoxide, no technical advantages, etc., to reduce the cost of production raw materials, reduce the reduction of secondary substitution Response, the effect of reducing energy consumption

Active Publication Date: 2009-07-29
HANGZHOU HEZE PHARMA TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As we all know, potassium tert-butoxide is expensive, its chemical properties are very active, and it is dangerous (it will explode with water). In addition, because the catalytic activity of potassium tert-butoxide is too strong, it is easy to produce two substitutions, and the obtained product Difficult to purify
Generally speaking, using potassium tert-butoxide as a catalyst for the condensation reaction has no technical advantage, the product quality is difficult to guarantee, and the production is dangerous and industrialization is difficult.

Method used

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  • Method for preparing high-purity cetirizine hydrochloride
  • Method for preparing high-purity cetirizine hydrochloride
  • Method for preparing high-purity cetirizine hydrochloride

Examples

Experimental program
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Effect test

Embodiment 1

[0034] In a 1000ml four-necked flask, add 100g of 4-[(4-chlorophenyl)phenyl-]1-hydroxyethylpiperazine, then add 175ml of DMSO, stir at room temperature until dissolved, then add 30g of caustic soda After stirring for 1 hour, slowly add 80g of sodium chloroacetate at 10°C to 20°C, finish adding in about 1 hour, and react at 30 to 40°C for 12 hours. TLC detects that the raw materials should be basically reacted completely. After the reaction is complete, add 500ml of water, stir for half an hour, then adjust the pH value to about 9.0 with 10% (w / w) hydrochloric acid, add 200ml of toluene, extract 3 times, and continue to use 10% (w / w) for the water layer. / w) hydrochloric acid to adjust the pH to about 7.5, continue to extract and wash 3 times with 200ml of toluene, continue to use 10% (w / w) hydrochloric acid to adjust the pH to about 4.0 for the aqueous layer, and use 200ml of dichloromethane After extraction three times, the organic layers were combined, and the dichloromethan...

Embodiment 2

[0036] In a 1000ml four-necked flask, add 100g of 4-[(4-chlorophenyl)phenyl-]1-hydroxyethylpiperazine, then add 175ml of DMF, stir at room temperature until dissolved, then add 40g of caustic soda After stirring for 1 hour, slowly add 80g of sodium chloroacetate at 5℃~10℃, finish adding in about 1 hour, and react at 20~30℃ for 12 hours. TLC detection of raw materials should basically complete the reaction. After the reaction is complete, add 500ml of water, stir for half an hour, then adjust the pH to about 9.0 with about 10% hydrochloric acid, add 200ml of ethyl acetate, extract 3 times, and continue to adjust the pH of the water layer with about 10% hydrochloric acid When the pH value is around 7.0, continue to extract and wash 3 times with 200 ml of ethyl acetate, continue to adjust the pH value of the aqueous layer to around 4.0 with about 10% hydrochloric acid, extract three times with 200 ml of dichloromethane, combine the organic layers, and concentrate under reduced pre...

Embodiment 3

[0038] In a 1000ml four-necked flask, add 100g of 4-[(4-chlorophenyl)phenyl-]1-hydroxyethylpiperazine, then add 175ml of DMSO, stir at room temperature until dissolved, then add 40g of hydroxide Potassium, after stirring for 1 hour, slowly add 80g of sodium chloroacetate at 10 ℃ ~ 15 ℃, add in about 1 hour, react at 25 ~ 35 ℃ for 12 hours, TLC detection of raw materials should basically complete the reaction. After the reaction is complete, add 500ml of water, stir for half an hour, then use about 10% hydrochloric acid to adjust the pH to about 9.5, add 200ml of toluene to extract 3 times, and continue to adjust the pH to 7.5 with about 10% hydrochloric acid for the water layer. Continue to extract and wash 3 times with 200ml of toluene, continue to adjust the pH value of the aqueous layer to about 4.0 with about 10% hydrochloric acid, extract 3 times with 200ml of dichloromethane, combine the organic layers, and concentrate the dichloromethane under reduced pressure to dryness...

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Abstract

The invention provides a preparation method of cetirizine hydrochloride with high purity. The method comprises: 4-[(4-chlorophenyl) phenyl]-1-hydroxyethyl piperazine and sodium chloroacetate are used as reaction substrates and alkali metal hydroxide is used as catalyst for the condensation reaction in organic solvent at 5-40 DEG C; when the condensation reaction is finished, cetirizine mother nucleus compounds obtained after the reaction are separated and the salt-forming reaction is carried out between the cetirizine mother nucleus compounds and hydrogen chloride gas. The cetirizine hydrochloride is obtained. The method of the invention has the advantages of simple technical process, easily obtained raw materials, safe operation, little produced three wastes and high purity of obtained cetirizine hydrochloride products and satisfies standards of British pharmacopeia and European pharmacopoeia.

Description

(1) Technical field [0001] The invention relates to a high-purity cetirizine hydrochloride (chemical name: 2-[2-[4-[(4-chlorophenyl) benzyl]-1-piperazinyl] ethoxy] acetic acid disalt The preparation method of acid salt) belongs to the technical field of medicine and chemical industry. (2) Background technology [0002] Cetirizine Hydrochloride has the structure shown in general formula 1 and is a new generation of H1 receptor antagonists. It was first developed by Belgian Chemical Union (UCB) and was first listed in Belgium in 1987. It is an effective selective oral potent antiallergic drug, which has the advantages of high selectivity to H1 receptors, long half-life, no sedative effect, and few adverse reactions in the central nervous system. It has been widely used in clinical treatment of respiratory system, skin and eye allergic diseases, and can be used in children. Therefore, its European market share has reached 27% after 18 months of listing. Since then, it has bee...

Claims

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Application Information

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IPC IPC(8): C07D295/088A61P37/08
Inventor 姜维斌倪晟
Owner HANGZHOU HEZE PHARMA TECH
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