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Method for preparing N-(2-Methylphenyl)-2-(propylamino)propa-namide

A technology of prilocaine hydrochloride and prilocaine, which is applied in the field of drug synthesis, can solve the problems of reduced yield, suboptimal synthesis process, unfavorable large-scale industrial production, etc., and achieves high yield, simple operation, and easy raw materials The effect

Active Publication Date: 2011-06-15
BENGBU BBCA MEDICINE SCI DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Use benzene or toluene as solvent in the existing prilocaine hydrochloride preparation method, use sodium carbonate as catalyzer or synthesize with pyridine as solvent or catalyzer, owing to have used such strong irritant as benzene and pyridine in the operating steps It is not conducive to large-scale industrial production, and the catalytic efficiency of sodium carbonate is not high
And because the synthesis process is not optimal, the yield is further reduced

Method used

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  • Method for preparing N-(2-Methylphenyl)-2-(propylamino)propa-namide
  • Method for preparing N-(2-Methylphenyl)-2-(propylamino)propa-namide
  • Method for preparing N-(2-Methylphenyl)-2-(propylamino)propa-namide

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Experimental program
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Effect test

Embodiment 1

[0027] The first step: amidation of o-toluidine

[0028] Add 30kg of o-methylaniline and 58kg of potassium carbonate into the reactor, add 150L of acetone to the reactor in an ice-water bath, slowly add 53kg of 2-chloropropionyl chloride dropwise, and control the internal temperature at 20-30°C for two hours The dropwise addition was completed; a large amount of solids were precipitated during the dropwise addition; reaction at room temperature. After detecting the disappearance of the raw material point (TLC detection, developing system: V dichloromethane: V petroleum ether=1: 3, add 2 drops of glacial acetic acid), stop the reaction, the reaction time is 2h; add 200L water in the reactor, and A large amount of solids were precipitated, and mechanical stirring was used to break the solids as much as possible, filtered, washed with 10 L of water each time, a total of 4 times, and dried, and the obtained solids were placed in a blast oven at 60 ° C for 11 hours to obtain 51 kg ...

Embodiment 2

[0034] The first step: amidation of o-toluidine

[0035] Add 30kg of o-methylaniline and 39kg of potassium carbonate into the reactor, add 150L of acetone to the reactor in an ice-water bath, slowly add 35kg of 2-chloropropionyl chloride dropwise, and control the internal temperature at 20-30°C for two hours The dropwise addition was completed; a large amount of solids were precipitated during the dropwise addition; reaction at room temperature. After detecting the disappearance of raw material points (TLC detection, developing system: V dichloromethane: V petroleum ether = 1: 3, add 2 drops of glacial acetic acid), stop the reaction, the reaction time is 3h; add 200L water in the reactor, and A large amount of solids were precipitated, and mechanical stirring was used to break the solids as much as possible, filtered, washed with 10 L of water each time, a total of 4 times, and dried, and the obtained solids were placed in a blast oven at 60 ° C for 11 hours to obtain 42 kg o...

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Abstract

The invention provides a method for preparing N-(2-Methylphenyl)-2-(propylamino)propa-namide. The method comprises the following steps: (1) carrying out amidation reaction based on o-toluidine as a raw material, 2-chloropropionyl chloride as an amidation reagent and potassium cardonate as a catalyst, and preparing an intermediate; (2) carrying out ammoniation reaction on the intermediate prepared in the step (1) and propylamine, so as to prepare crude prilocainum; and (3) dissolving the prepared crude prilocainum in ethyl acetate or acetone, and regulating the pH value to 1-3 with more than or equal to 35% concentrated hydrochloric acid so as to salify. The method has the advantages that harsh reaction conditions such as high temperature, high pressure and the like do not exist in the process route, raw material is available, operation is simple, yield is high, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for preparing prilocaine hydrochloride, which belongs to the field of drug synthesis. Background technique [0002] Prilocaine is used in various surgical anesthesia such as epidural, block and infiltration. The medicinal effect of this medicine is better than that of procaine, and the intensity and speed of action are similar to those of lidocaine, but the action time is longer, the toxicity is less, and because of the fast metabolism, the accumulation is also small. Prilocaine hydrochloride is the hydrochloride salt of prilocaine, which can improve its solubility in water and the stability of solid. [0003] Use benzene or toluene as solvent in the existing prilocaine hydrochloride preparation method, use sodium carbonate as catalyzer or synthesize with pyridine as solvent or catalyzer, owing to have used such strong irritant as benzene and pyridine in the operating steps It is not conducive to large-scale industri...

Claims

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Application Information

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IPC IPC(8): C07C231/12C07C237/04
Inventor 胡媛郑爱张亚
Owner BENGBU BBCA MEDICINE SCI DEV
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