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Preparation method of dibucaine hydrochloride

Dibucaine hydrochloride and Dibucaine technology, applied in the field of medicine and chemical industry, can solve problems such as low purity and low yield of Dibucaine hydrochloride

Active Publication Date: 2017-03-15
KUNMING YUANRUI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of this invention is to provide a kind of preparation method of Dibucaine Hydrochloride, by optimizing preparation technology, to solve the problem of low purity and low yield of Dibucaine Hydrochloride in industrial production

Method used

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  • Preparation method of dibucaine hydrochloride

Examples

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Effect test

Embodiment 1

[0060] A. Synthesis of 2-chloro-4-acylchloroquinoline 1

[0061] Add 18.9 grams of 2-hydroxy-4-quinoline carboxylic acid to a 250 ml three-necked flask at room temperature, add 15.3 grams of thionyl chloride dropwise under stirring with 150 ml of toluene, heat up to 60°C for 3 hours, cool to 30°C, Concentrate under reduced pressure, add a little toluene, and continue to concentrate under reduced pressure to dryness. 19.5 g of oil was obtained, yield 91.3%.

[0062] B. Synthesis of 2-chloro-N-[2-(diethylamino)ethyl]-4-quinoline carboxamide

[0063] Dilute the oil obtained above with 200ml of toluene and add it to a 500ml three-necked flask, then add 10g of N,N-diethyldiethylamine, stir at 60°C, cool down to room temperature after the reaction is complete, add water and stir for 30 minutes , liquid separation, the organic layer was washed twice with water, washed once with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was spin-dried to obtain...

Embodiment 2

[0069] A. Synthesis of 2-chloro-4-acylchloroquinoline

[0070] Add 11 grams of 2-hydroxy-4-quinoline carboxylic acid to a 250 ml three-necked flask at room temperature, add 11.2 grams of thionyl chloride dropwise under stirring with 110 ml of toluene, heat up to 45°C for 2.5 hours, cool to 25°C, reduce Concentrate under reduced pressure, add a little toluene, and continue to concentrate under reduced pressure to dryness to obtain 15.4 g of oil, with a yield of 83.3%;

[0071] B. Synthesis of 2-chloro-N-[2-(diethylamino)ethyl]-4-quinoline carboxamide

[0072] Dilute the oil obtained above with 300 ml of toluene and add it to a 500 ml three-necked flask, then add 7 grams of N,N-diethyldiethylamine, stir at 80°C, cool to room temperature after the reaction is complete, add water and stir for 25 minutes , liquid separation, the organic layer was washed twice with water, washed once with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was spin-drie...

Embodiment 3

[0078] A. Synthesis of 2-chloro-4-acylchloroquinoline

[0079]Add 28.9 grams of 2-hydroxy-4-quinoline carboxylic acid to a 250 ml three-necked flask at room temperature, add 19.2 grams of thionyl chloride dropwise under stirring with 190 ml of toluene, heat up to 75°C for 3.5 hours, cool down to 35°C, reduce Concentrate under reduced pressure, add a little toluene, and continue to concentrate under reduced pressure to dryness. 19.5 g of oil was obtained, yield 88.3%.

[0080] B. Synthesis of 2-chloro-N-[2-(diethylamino)ethyl]-4-quinoline carboxamide

[0081] Dilute the oil obtained above with 220ml of toluene and add it to a 500ml three-necked flask, then add 14.5g of N,N-diethyldiethylamine, stir at 70°C, cool down to room temperature after the reaction is complete, add water and stir for 40 minutes , liquid separation, the organic layer was washed twice with water, washed once with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was spin-dr...

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Abstract

The invention discloses a preparation method of dibucaine hydrochloride, comprising chlorinating 2-hydroxy-4-quinolinecarboxylic acid as raw material, amidating to obtain 2-chloro-N-[2-(diethylaminoethyl)ethyl]-4-quinolinecarboxamide (cinchoamide), dropwise adding acetone hydrochloride solution to cinchoamide to obtain dibucaine, and salifying to obtain dibucaine hydrochloride. The preparation method has the advantages that product purity and yield are increased, the cost is greatly reduced, the method is simplified, and the method is more suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and in particular relates to a preparation method of dibucaine hydrochloride. Background technique [0002] Dibucaine Hydrochloride is a drug used for local anesthesia. It can be used for epidural anesthesia and spinal anesthesia. It is easy to pass through the mucous membrane and is also used for surface anesthesia. However, it is rarely used for infiltration anesthesia because of its high toxicity. . Dibucaine hydrochloride as an anesthetic has the characteristics of long duration of anesthesia. For epidural anesthesia and spinal anesthesia, dibucaine hydrochloride is used in 0.2%-0.25% solution, with a total dose of 7.5-12mg. Use 0.05% to 0.2% for surface anesthesia, and 0.01% to 0.1% for infiltration anesthesia. It can be combined with epinephrine during infiltration anesthesia, and the total dose should not exceed 15mg. [0003] At present, there are mainly two synthetic route...

Claims

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Application Information

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IPC IPC(8): C07D215/50
CPCC07D215/50
Inventor 王高华牛树伟王艳昌
Owner KUNMING YUANRUI PHARMA
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