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Synthetic method of cinchocaine

Dibucaine and the technology of its synthetic method are applied in the field of medicine and chemical industry, which can solve the problems of unfavorable industrial production, strong alkalinity of sodium butoxide, potential safety hazards, etc., and achieve the effects of improved safety, environmental protection of the synthetic process, and reduction of by-products

Inactive Publication Date: 2018-05-08
山东诚汇双达药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These reports all adopt metal sodium to prepare sodium n-butoxide when synthesizing Dibucaine, then react synthetic Dibucaine with 2-chloro-N-[2-(diethylamino) ethyl]-4-quinoline formamide, the There is a great potential safety hazard in the preparation method, because the chemical properties of metal sodium are very active, and it reacts violently with oxygen and water at normal temperature, and it is easy to react violently with inorganic substances such as water and oxygen in the post-treatment process to cause serious consequences such as explosions, and Ding Sodium alkoxide has strong alkalinity, more impurities are produced in the reaction process, and the yield is lower, which is not conducive to industrial production

Method used

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  • Synthetic method of cinchocaine

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Experimental program
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Effect test

Embodiment 1

[0030] The sodium hydroxide of 150g 2-chloro-N-[2-(diethylamino) ethyl]-4-quinoline formamide, 39g is added in the solution of 90g n-butanol, 600g n-hexane, slowly Raise the temperature to reflux for water separation, after the water separation is completed, cool down to room temperature, add deionized water and stir for 1 hour, stand still for 0.5 hours, separate the water phase, add deionized water to the organic phase and stir for 0.5 hours, separate the liquid to remove the water phase, The organic phase was stirred and crystallized at 0-10°C for 8 hours, filtered and dried to obtain 162.5 g of dibucaine fine product, with a molar yield of 96.4% and a liquid phase purity of 99.9%.

Embodiment 2

[0032] The sodium hydroxide of 150g 2-chloro-N-[2-(diethylamino) ethyl]-4-quinoline formamide, 39g is added in the solution of 90g n-butanol, 600g sherwood oil, slowly Raise the temperature to reflux for water separation. After the water separation is completed, cool down to room temperature, add deionized water and stir for 1 hour, and keep stratifying for 0.5 hours. Separate the liquid to remove the water phase. Then add deionized water to the organic phase and stir for 0.5 hours. The aqueous phase was removed by liquid separation, and the organic phase was stirred and crystallized at 0-10°C for 8 hours, filtered and dried to obtain 160.3 g of fine dibucaine, with a molar yield of 95.1% and a liquid phase purity of 99.9%.

Embodiment 3

[0034] 150kg of 2-chloro-N-[2-(diethylamino) ethyl]-4-quinoline carboxamide, 135kg of salt of wormwood are added in the solution of 90kg n-butanol, 600kg of toluene, slowly warming up to Reflux water separation, after water separation is completed, cool down to room temperature, add deionized water and stir for 1 hour, static layering for 2 hours, liquid separation to remove the water phase, add deionized water to the organic phase and stir for 0.5 hours, static layering for 0.5 hours, liquid separation and removal The water phase and the organic phase were stirred and crystallized at 0-10°C for 8 hours, filtered and dried to obtain 158.0 g of fine dibucaine, with a molar yield of 93.8% and a liquid phase purity of 99.8%.

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Abstract

The invention belongs to the technical field of pharmaceutical and chemical industry, in particular to a synthetic method of cinchocaine. The method comprises the following step of synthesizing 2-chloro-N-[2-(diethylamino)ethyl]-4-quinoline formamide, n-butyl alcohol and sodium hydroxide serving as raw materials to obtain the cinchocaine. The synthetic method has the advantages of high molar yield, low cost, safety, environmental friendliness and the like, and is more suitable for industrialization.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical industry, and in particular relates to a method for synthesizing dibucaine, which has the characteristics of safety and environmental protection. Background technique [0002] Dibucaine Chinese aliases dibucaine, nuvacaine, savcaine, chemical name 2-butoxy-N-[2-(diethylamino)ethyl]-4-quinoline carboxamide, CAS No.: 85-79-0, its structural formula is: [0003] . [0004] Dibucaine is a local anesthetic drug that can be used for epidural anesthesia and spinal anesthesia. It is easy to pass through the mucous membrane and is also used for topical anesthesia. However, due to its high toxicity, it is rarely used for infiltration anesthesia. Dibucaine hydrochloride as an anesthetic has the characteristics of long anesthetic action time, and the local anesthetic effect is 22-25 times greater than that of procaine. Dibucaine hydrochloride is an amide long-acting local anesthetic. Its te...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/50
CPCC07D215/50
Inventor 王庭见杨彦军王文新胡俊峰李春杰
Owner 山东诚汇双达药业有限公司
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