Preparation method of articaine hydrochloride

A technology for articaine hydrochloride and amidation, which is applied in the field of preparation of articaine hydrochloride, can solve the problems of cumbersome operation, harsh reaction conditions, and low reaction yield, and achieve high yield, simple operation, and low raw material Easy to get effect

Active Publication Date: 2011-05-18
BENGBU BBCA MEDICINE SCI DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Among the synthetic methods reported in relevant literature, articaine hydrochloride has many synthetic steps, complex operations, harsh reaction conditions, and low yield of reaction
Because its synthesis process does not reach optimum in the prior art, cause yield to further reduce

Method used

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  • Preparation method of articaine hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The first step: amidation of methyl 4-methyl-3-aminothiophene-2-carboxylate

[0033] Add 1600ml of dichloromethane into the reaction kettle, add 800g of 4-methyl-3-aminothiophene-2-carboxylic acid methyl ester (yellow) with a funnel, stir to dissolve the solid. Use an ice-water bath to lower the reaction kettle to about 10°C, add 700ml of triethylamine with stirring, and then slowly add 580ml of 2-chloropropionyl chloride dropwise, a large amount of white smoke and a large amount of white solids can be seen in the reaction vessel. After the dropwise addition was completed, the ice-water bath was naturally warmed up to room temperature, and reacted for 5 hours.

[0034] Slowly pour the resulting reaction solution into the barrel, add 1600ml of dichloromethane, add 1600ml of distilled water, stir mechanically, and carefully add Na 2 CO 3 Solid, to neutralize excess 2-chloropropionyl chloride, adjust the pH to be alkaline (pH 7.5-9). During this process, a large amount ...

Embodiment 2

[0041] The same operation was performed as in Example 1, only 700 ml of triethylamine used in the amidation reaction step was replaced with 960 g of potassium carbonate, and the others were kept unchanged to obtain 850 g of intermediate, the yield of this step was 70%, and the melting range: 97-98 ° C. The reaction was continued to obtain 830 g of articaine oil, and the yield of this step was 90%. After salt formation, 795g of the final product was obtained, with a purity of 99.1%, and a yield of 85% in this step. The infrared spectrum of the product obtained is similar to the final product of Example 1.

Embodiment 3

[0043] The same operation was carried out as in Example 1, only the 2-chloropropionyl chloride used in the amidation reaction step was replaced with 2-chloropropionyl bromide, and the others were kept unchanged to obtain 1076 g of the intermediate. 1020 g of the final product was obtained, the melting range was 118-119° C., the purity was 99.3%, and the yield was about 85%. The infrared spectrum of the product obtained is similar to the final product of Example 1.

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Abstract

The invention discloses a preparation method of articaine hydrochloride. The method comprises the following steps: carrying out amidation reaction on 4-methyl-3-aminothiophene-2-methyl formate utilized as a raw material and 2-chloro propionyl chloride; then carrying out the ammoniation reaction with propylamine; and carrying out salification reaction with concentrated hydrochloric acid, thus obtaining the articaine hydrochloride. The invention has the following advantages: the process route of the preparation method is suitable for industrial production, the rigorous reaction conditions are avoided, raw materials are easy to obtain, the operation is simple, and the yield coefficient is high.

Description

technical field [0001] The invention relates to a preparation method of articaine hydrochloride. Background technique [0002] Articaine hydrochloride is an amide local injection anesthetic, which can block the nerve conduction along the nerve fibers at the injection site and act as a local anesthetic. Adding 1 / 100,000 epinephrine to the articaine solution can be used to constrict local blood vessels, delay anesthetics from entering the systemic circulation, maintain local tissue concentration, and at the same time obtain a surgical field with minimal bleeding. Local anesthesia occurs 2-3 minutes after administration and lasts for about 60 minutes. During pulp anesthesia, the time can be shortened by 2-3 times. Because of its good anesthesia effect, the market demand is relatively large. [0003] Among the synthetic methods reported in relevant literature, the synthetic steps of articaine hydrochloride are many, the operation is tedious, the reaction conditions are harsh,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/38
Inventor 郑爱张亚胡媛张杰杨志强李立标
Owner BENGBU BBCA MEDICINE SCI DEV
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