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Synthesis process of roxatidine acetate hydrochloride

A technology of roxatidine acetate and a synthesis method, which is applied in directions such as organic chemistry, can solve the problems of low purity of the target compound, complicated operation, difficult application and the like, and achieves a technology that is beneficial to industrial development and application, improves the purity, and has a simple synthesis process. Effect

Inactive Publication Date: 2007-06-27
LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis method is complicated to operate, carcinogenic substances are used in the synthesis process, the utilization rate of atoms is low, and the purity of the target compound is low, so it is difficult to apply in practice

Method used

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  • Synthesis process of roxatidine acetate hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Synthesis of 3-piperidylmethylphenol

[0028] Add 20g of m-hydroxybenzaldehyde, 110ml of methanol, and 34g of piperidine into a three-necked flask, and stir at room temperature for 0.5 hours to dissolve completely. Add 8.8g KBH within 1 hour 4 , continue to stir at room temperature for 1 hour, the reaction resultant is concentrated under reduced pressure, is cooled to room temperature, adds 200ml 3N hydrochloric acid to dissolve, extracts with ethyl acetate, ammoniacal liquor basifies the aqueous layer, separates out white solid, filters, and can obtain target object (I ) 27g. m.p.135℃~138℃.

Embodiment 2

[0030] Synthesis of 3-piperidylmethyl-phenoxypropylamine

[0031] 20g of 3-chloropropylamine was dissolved in 45ml of 3N NaOH solution (containing 10% NaCl), and extracted with 350ml of toluene.

[0032] Add 19g of 3-piperidinylmethylphenol, 4.5g of NaOH, 45ml of DMSO, and 25ml of toluene into a three-necked flask with a water separator, reflux at 110°C to separate the water, and after no water is removed, add the 3-chloropropylamine toluene extract, and complete the addition Afterwards, reflux at 110°C to 120°C for 4 hours. After completion, NaCl was filtered off, and the filtrate was concentrated under reduced pressure. Add the mixed solvent of 400ml ethanol-acetone-ethyl acetate (volume ratio=5:2:3), dropwise add 2-methylsuccinic acid-ethanol saturated solution therein, separate out white powder, filter out and add water to dissolve, use 0.8NNaOH solution adjusts the pH value between 6.0 and 8.0, extracts impurities with toluene, then uses 1.5NNaOH solution to adjust the p...

Embodiment 3

[0034] Synthesis of Acetoxyacetyl Chloride

[0035] Dissolve 35g of glycolic acid in 50ml of DMF, add 36g of acetyl chloride dropwise with stirring at room temperature, heat up to 50°C for 1.5 hours after the dropwise addition, concentrate the reaction solution under reduced pressure, and add chloroform-SOCl to the concentrate 2 The solution was heated up to 50°C with stirring, kept for 2 hours, then distilled under reduced pressure, and fractions at 67°C to 77°C / 1kPa were collected.

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Abstract

The present invention discloses synthesis process of roxatidine acetate hydrochloride. The synthesis process includes the following steps: the reducing aminolysis reaction of m-hydroxy benzaldehyde as the initial material and piperidine to obtain 3-piperidino methyl phenol, the condensation of 3-piperidino methyl phenol and 3-halo propylamine to obtain 3-piperidino methyl-phenoxy propylamine, the amidation of 3-piperidino methyl-phenoxy propylamine and acetyloxy acetyl chloride to obtain 2-acetyloxy-N-[3-[3-(1- piperidino methyl phenyl) oxy] propyl] acetamide, and introducing dry HCl gas into anhydrous alcohol-acetone solution of 2-acetyloxy-N-[3-[3-(1- piperidino methyl phenyl) oxy] propyl] acetamide to obtain the ultimate compound 2-acetyloxy-N-[3-[3-(1- piperidino methyl phenyl) oxy] propyl] acetamide hydrochloride. The process is simple, high in target compound and favorable to industrial production.

Description

technical field [0001] What the present invention relates to is the synthetic method of roxatidine acetate hydrochloride. Background technique [0002] Roxatidine acetate hydrochloride is a new generation of histamine H 2 Receptor antagonists are mainly used for the prevention and treatment of digestive system diseases caused by hypersecretion of gastric acid. Roxatidine acetate hydrochloride, the chemical name is 2-acetoxy-N-[3-[3-(1-piperidinylmethylphenyl)oxy]propyl]acetamide hydrochloride, is New Generation Histamine H 2 Receptor antagonists can effectively inhibit the secretion of gastric acid, significantly inhibit the secretion of gastric acid caused by food, histamine or pentagastrin and other stimuli, and reduce the acidity. The pharmacology, toxicology, pharmacokinetics and clinical studies of the drug have been conducted abroad. This type of drug occupies a dominant position in the domestic gastric ulcer drug market, with a market share of more than 30%. [0...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/096
Inventor 刘树法王健康陈方孙克仁
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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