Synthetic method of tropicamide

A synthetic method, the technology of tropic amide, applied in the direction of organic chemistry, etc., can solve the problems of poor stability of intermediate products, difficult promotion and application, and increased cost

Inactive Publication Date: 2018-03-06
上海泰坦科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] CN 103159672 A discloses a preparation method of tropic amide, which solves the problem of poor stability of the intermediate product, but the yield is low (basically maintained below 50%), and there are many impurities in the intermediate reaction. Increase cost, difficult to promote and apply

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  • Synthetic method of tropicamide

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Experimental program
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Effect test

Embodiment 1

[0059] 1) Using 10mol of diethyl phenylmalonate as raw material, hydrolysis reaction occurs in an inorganic alkali solvent to obtain intermediate product A, wherein the pH of the hydrolysis reaction is 8, the temperature is 0°C, and the time is 0.5h. The molar ratio of diethyl malonate and inorganic base is 1:2;

[0060] 2) intermediate product A and sulfur oxychloride carry out acylation reaction in methylene chloride solvent, obtain intermediate product B, the mol ratio of intermediate product A and sulfur oxychloride is 1:2, and the temperature of described acylation reaction is 0°C, the time is 2h;

[0061] 3) Intermediate product B and 20mol N-ethyl-4-methylpyridinamine undergo condensation reaction in tetrahydrofuran solvent to obtain intermediate product C, the molar ratio of intermediate product B to N-ethyl-4-methylpyridinamine is 1:1.5, the temperature of the condensation reaction is 5°C, and the time is 1h;

[0062] 4) The intermediate product C and 40 mol of calc...

Embodiment 2

[0064] 1) Using 10mol of diethyl phenylmalonate as a raw material, hydrolysis reaction occurs in an inorganic alkali solvent to obtain intermediate product A, wherein the pH of the hydrolysis reaction is 12, the temperature is 34 ° C, and the time is 8 hours. The mol ratio of diethyl diacid and inorganic base is 1:8;

[0065] 2) intermediate product A and sulfur oxychloride carry out acylation reaction in methylene chloride solvent, obtain intermediate product B, the mol ratio of intermediate product A and sulfur oxychloride is 1:20, the temperature of described acylation reaction is 60℃, the time is 22h;

[0066] 3) Intermediate product B and 100mol N-ethyl-4-picoline amine undergo condensation reaction in tetrahydrofuran solvent to obtain intermediate product C, the molar ratio of intermediate product B to N-ethyl-4-picoline amine is 1:6, the temperature of the condensation reaction is 20°C, and the time is 20h;

[0067] 4) The intermediate product C and 300 mol of calcium...

Embodiment 3

[0069] 1) Using 10mol of diethyl phenylmalonate as a raw material, hydrolysis reaction occurs in an inorganic alkali solvent to obtain intermediate product A, wherein the pH of the hydrolysis reaction is 10, the temperature is 18°C, and the time is 4h. The mol ratio of diethyl diacid and inorganic base is 1:5;

[0070] 2) intermediate product A and sulfur oxychloride carry out acylation reaction in methylene chloride solvent, obtain intermediate product B, the mol ratio of intermediate product A and sulfur oxychloride is 1:11, the temperature of described acylation reaction is 30℃, the time is 12h;

[0071] 3) Intermediate product B and 60mol N-ethyl-4-methylpyridinamine undergo condensation reaction in tetrahydrofuran solvent to obtain intermediate product C, the molar ratio of intermediate product B to N-ethyl-4-methylpyridinamine is 1:3.5, the temperature of the condensation reaction is 12°C, and the time is 10h;

[0072] 4) The intermediate product C and 170 mol of potas...

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Abstract

The invention relates to a production method of chemical medicines and particularly relates to a synthetic method of tropicamide. The synthetic method comprises the steps of carrying out hydrolysis and acylation on the raw material, namely diethyl phenylmalonate, condensing diethyl phenylmalonate with N-ethyl-4-methylpyridine amine, and generating reduction reaction with hydroboron, so as to obtain tropicamide. The synthetic method has the beneficial effects that the raw material cost is low, the properties of an intermediate product are stable, impurities are few, the operation steps such aspurification are reduced, and the process is simplified; reaction conditions are safe and mild, extremely toxic substances are not introduced, and the industrial amplified production is promoted; andby optimizing the raw material ratio, the total yield of the reaction is increased to be 65% and is greatly increased, and the production cost is lowered.

Description

technical field [0001] The invention relates to the field of chemical medicines, in particular to a method for synthesizing a compound, in particular to a method for synthesizing tropicamide. Background technique [0002] Tropinamide is an anticholinergic drug and a parasympathetic nerve inhibitor. In the field of ophthalmology, it is the preferred mydriatic agent for fundus examination and diagnosis, and it also has the effect of ciliary muscle anesthesia. It was first synthesized by Roche Company in 1955 and collected in the US Pharmacopoeia, British Pharmacopoeia and Japanese Pharmacopoeia respectively. In addition to being used alone clinically, it is mostly used in compound preparations. Japan's Santen Pharmaceutical Co., Ltd. uses a compound preparation of 0.5% tropicamide and 0.5% phenylephrine hydrochloride. The structure of tropicamide is similar to that of atropine, so it has the similar pharmacological characteristics of atropine and is used clinically, such as ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/40
CPCC07D213/40
Inventor 谢应波张庆张华徐肖冰罗桂云张维燕
Owner 上海泰坦科技股份有限公司
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