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A kind of synthesis technique of dyclonine hydrochloride

A technology of dyclonine hydrochloride and synthesis process, applied in the direction of organic chemistry and the like, can solve the problems of long process reaction time, high toxicity of reagents, long distillation time, etc., and achieve the effects of shortening reaction time, short reaction time and simple steps

Active Publication Date: 2020-05-01
GUIZHOU MAQIKA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this process has improved the original synthesis process, there are still technical problems such as long process reaction time, high toxicity of reagents, long distillation time during purification, and low yield.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] (1) Preparation of phenylbutyl ether: add 150g of NaOH and 180g of phenol to the reaction flask, add anhydrous ethanol solvent, stir to dissolve, add 280g of bromo n-butane, heat to 40 ℃ to react for 2h to obtain the reaction solution, the reaction solution The organic layer was separated, washed with water and saturated NaCl solution, dried with anhydrous sodium sulfate, and the solvent was spin-dried under reduced pressure to obtain 258 g of phenbutyl ether with a yield of 90% and a content of 96%.

[0029] (2) Preparation of 1-(4-butoxyphenyl)-3-chloropropyl-1-one: add dichloromethane into the reaction flask, add 134g 3-chloropropionyl chloride and 160g phenbutyl ether, add 240g aluminum chloride, stirred for 1 hour at 3°C, added water, separated the organic layer, extracted the aqueous layer with dichloromethane, combined the organic layers, washed with water and saturated sodium bicarbonate, dried with anhydrous sodium sulfate, and evaporated under reduced pressure Dr...

Embodiment 2

[0033] Step (1) The reaction temperature is 80° C., the reaction time is 5 hours, and the weight of the obtained phenbutyl ether is 255 g, and the yield is 88.9%.

[0034] Step (2) The reaction temperature is 50° C., the reaction time is 5 hours, and 205 g of 1-(4-butoxyphenyl)-3-chloropropyl-1-one is obtained, and the yield is 80%.

[0035] Step (3) The reaction temperature is 120° C., the reaction time is 5 hours, and 346 g of crude dyclonine hydrochloride is obtained.

[0036] Step (4) Add activated carbon to reflux and decolorize for 5 hours to obtain 251g of white crystal dyclonine hydrochloride product, the content is 99.3%, the yield is 75%

[0037] The other steps are the same as in Example 1.

Embodiment 3

[0039] Step (1) The reaction temperature is 70° C. and the reaction time is 4 hours. The weight of the obtained phenbutyl ether is 261 g, and the rate is 90.9%.

[0040] Step (2) The reaction temperature is 15° C., the reaction time is 2 h, and 215 g of 1-(4-butoxyphenyl)-3-chloropropyl-1-one is obtained, and the yield is 83.9%.

[0041] Step (3) The reaction temperature is 90° C. and the reaction time is 3 hours to obtain 350 g of crude dyclonine hydrochloride.

[0042] Step (4) Add activated carbon to reflux and decolorize for 2h to obtain 263g of white crystal dyclonine hydrochloride fine product, the content is 99.3%, the yield is 79%

[0043] The other steps are the same as in Example 1.

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PUM

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Abstract

The invention discloses a process for synthesizing dyclonine hydrochloride. The process comprises the following steps: by taking phenol as a start raw material, firstly, synthesizing phenate butyl with n-butyl bromide; secondly, under the catalysis action of chloride, reacting the phenate butyl with 3-chloropropionyl chloride so as to obtain 3-chlorine-4'-butoxy propiophenone; and further reacting 3-chlorine-4'-butoxy propiophenone with piperidine hydrochloride under the action of triethylamine, thereby obtaining the dyclonine hydrochloride. As an organic solvent is adopted as a solvent, the process is short in reaction time, low in temperature, small in impurity and high in yield, meanwhile the process is simple, no distillation is needed, high-purity phenate butyl is prepared directly, no toxic acetic anhydride is used, and industrial large-scale production is facilitated.

Description

Technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a synthetic process of dyclonine hydrochloride. Background technique [0002] Dyclonine hydrochloride (Dyclonine hydrochloride) is chemically named 4-butoxy-β-piperidinyl phenylacetone hydrochloride. It is a local anesthetic with fast onset, long acting time, small side effects and high safety. ; Also used to treat male premature ejaculation. [0003] There are two existing synthetic routes for dyclonine hydrochloride. One is Babu, B. Ramesh reported in Indian Patent IN172270A (Publication Date May 29, 1993, CA124: 289276). Ketone is the starting material, firstly react with bromobutane to synthesize p-butoxyacetophenone, and then with piperidine and aqueous formaldehyde solution to synthesize dyclonine hydrochloride under the catalysis of concentrated hydrochloric acid. Another synthetic route is the one disclosed by the patent of Yangzijiang Pharmaceutical Group Co., Ltd. (CN...

Claims

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Application Information

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IPC IPC(8): C07D295/108
CPCC07D295/108
Inventor 张芝庭张涛涛
Owner GUIZHOU MAQIKA PHARMA
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