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Dyclonine hydrochloride synthesizing method

A technology of dyclonine hydrochloride and a synthesis method, applied in the direction of organic chemistry and the like, can solve the problems of low conversion rate of hydroxyacetophenone, unable to recycle the solvent, increase the operation process, etc., and achieves convenient post-processing, easy industrial production, Simple and safe operation

Inactive Publication Date: 2017-10-10
CHANGZHOU TIANHUA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This route has fewer reaction steps, mild reaction conditions, and simple operation. However, in the actual operation process of the first step reaction, because n-bromobutane is insoluble in water, the whole system belongs to a two-phase reaction, resulting in a high conversion rate of p-hydroxyacetophenone. Low, in the second step reaction, it is necessary to re-prepare the alcohol solution of hydrogen chloride isopropanol, which increases the operation process and causes the solvent to be unable to be recycled, and the production cost is relatively large

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Weigh p-hydroxyacetophenone (136.2g, 1.0mol, 1.0eq), water (680mL), benzyltriethylammonium chloride (13.9g, 0.05mol, 0.05eq) into a 2L four-necked flask, Stir to dissolve and clarify, add NaOH (72g, 1.8mol, 1.8eq), stir to dissolve completely, then slowly add n-bromobutane (178.1g, 1.3mol, 1.3eq) at 70°C, add dropwise for 1h, and then keep warm for reaction 6h, TLC monitoring raw material disappears (V PE / EA =15:1), stop the reaction, cool to room temperature, stand still and separate the liquids, use ethyl acetate (200mL*2) for the aqueous phase, combine the organic phases, wash with dilute hydrochloric acid until neutral, and wash with saturated brine, anhydrous sulfuric acid Sodium was dried, the solvent was recovered under normal pressure, and 176 g of colorless transparent liquid 4-n-butoxyacetophenone was collected by distillation under reduced pressure, with a yield of 91.5%.

[0023] 4-n-butoxyacetophenone (154g, 0.8mol, 1.0eq), piperidine hydrochloride (146...

Embodiment 2

[0026] Weigh p-hydroxyacetophenone (204g, 1.5mol, 1.0eq), water (900mL), PEG-2000 (20g) into a 2L four-neck flask, stir to dissolve and clarify, add NaOH (96g, 2.4mol, 1.6 eq), stirred and dissolved completely, then slowly added n-bromobutane (247g, 1.8mol, 1.2eq) at 50°C, added dropwise for 1h, then incubated for 8h, and TLC monitored the disappearance of the raw material (V PE / EA =15:1), stop the reaction, cool to room temperature, stand still and separate the liquids, use ethyl acetate (300mL*2) for the aqueous phase, combine the organic phases, wash with dilute hydrochloric acid until neutral, and wash with saturated brine, then wash with anhydrous sulfuric acid The sodium was dried, the solvent was recovered under normal pressure, and 274 g of colorless transparent liquid 4-n-butoxyacetophenone was collected by distillation under reduced pressure, with a yield of 95.1%.

[0027] Dissolve 4-n-butoxyacetophenone (154g, 0.8mol, 1.0eq), piperidine hydrochloride (146g, 1.2m...

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PUM

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Abstract

The invention discloses a dyclonine hydrochloride synthesizing method and belongs to the field of chemical synthesis. The dyclonine hydrochloride synthesizing method reacting p-hydroxyacetophenone with n-butyl bromide in an alkali system and under the condition of phase transfer catalysts to synthesize p-butoxyacetophenone; performing Mannich reaction on the p-butoxyacetophenone, paraformaldehyde and piperidine hydrochloride under acidic conditions to synthesize crude dyclonine hydrochloride, and performing a refining process to obtain pure dyclonine hydrochloride. The purity of the refined pure dyclonine hydrochloride can reach up to 99.7%. The dyclonine hydrochloride synthesizing method is simple in operation and applicable to industrial production.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and relates to a synthesis method of dyclonine hydrochloride. Specifically, the method uses p-hydroxyacetophenone and n-bromobutane as raw materials to obtain crude dyclonine hydrochloride through etherification and Mannich reaction. Then it is purified to obtain pure dyclonine hydrochloride, which is a preparation method with short synthetic route, simple operation and suitable for industrial production. Background technique [0002] Dyclonine hydrochloride (dyclonine hydrochloride), the chemical name is 4-butoxy-3-piperidinyl propiophenone hydrochloride, is a commonly used local anesthetic in clinical practice, has strong penetrating power to mucous membrane, and has onset effect It is fast, long-lasting, low in adverse reactions, and high in safety. It is clinically used for local lubricating anesthesia. At the same time, it has also been reported that it can be used for the treatment of male...

Claims

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Application Information

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IPC IPC(8): C07D295/108
CPCC07D295/108
Inventor 李光文李剑平倪国成
Owner CHANGZHOU TIANHUA PHARMA
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