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Preparation method of dopamine hydrochloride

A technology of dopamine hydrochloride and dobutamine hydrochloride, which is applied in the field of medicinal chemistry, can solve the problems of harsh reaction conditions, high cost of decarboxylase, and unsuitability for industrial production, and achieve stable properties, not easy to be oxidized and degraded, and conducive to the control of impurities Effect

Active Publication Date: 2020-11-13
山东达冠医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction conditions of this method are harsh, and the cost of decarboxylase is relatively high, so it is not suitable for industrial production

Method used

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  • Preparation method of dopamine hydrochloride
  • Preparation method of dopamine hydrochloride
  • Preparation method of dopamine hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] A kind of preparation method of dopamine hydrochloride, concrete steps are:

[0037] 1. Synthesis of 3,4-dimethoxy-β-nitrostyrene

[0038] Add 6.8g of methylamine hydrochloride, 166.2g of veratraldehyde, 73.3g of nitromethane and 900ml of ethanol into a 2L three-necked flask, stir and dissolve, add dropwise 11.11g of triethylamine, and condense with stirring at room temperature. During the reaction, solid Gradually precipitate out. After the reaction, filter with suction, wash the filter cake with a small amount of cold ethanol, and dry under vacuum at 40°C to obtain 193.1 g of light yellow solid 3,4-dimethoxy-β-nitrostyrene, with a yield of 92.1%.

[0039] 2. Synthesis of 3,4-dimethoxyphenethylamine

[0040] Add 190.0g of 3,4-dimethoxy-β-nitrostyrene, 5% palladium carbon (19.0g, 50% water content), 572.2g of ammonium formate, and 1350ml of methanol into a 2L three-necked flask, under nitrogen protection, and stir. Raise the temperature to 60-65°C and react for 6-8 h...

Embodiment 2

[0046] A kind of preparation method of dopamine hydrochloride, concrete steps are:

[0047] 1. Synthesis of 3,4-dimethoxy-β-nitrostyrene

[0048] Add 10g of 30% methylamine ethanol solution, 166.2g of veratraldehyde, 73.3g of nitromethane and 900ml of ethanol into a 2L three-necked flask, stir, dissolve, and condense with stirring at room temperature. During the reaction, solids gradually precipitate out. After the reaction, filter with suction, wash the filter cake with a small amount of cold ethanol, and dry under vacuum at 40°C to obtain 186.5 g of light yellow solid 3,4-dimethoxy-β-nitrostyrene with a yield of 89.1%.

[0049] 2. Synthesis of 3,4-dimethoxyphenethylamine

[0050]Add 180.0g of 3,4-dimethoxy-β-nitrostyrene, 5% palladium carbon (18.0g, 50% water content), and 900ml of methanol into a 3L three-necked flask, protect with nitrogen, stir, and control the temperature for 20-30 ℃, add 1000.0 g of triethylsilane dropwise, and keep the reaction for 4 to 5 hours after...

Embodiment 3

[0056] A kind of preparation method of dopamine hydrochloride, concrete steps are:

[0057] 1. Synthesis of 3,4-dimethoxy-β-nitrostyrene

[0058] Add 6.8g of methylamine hydrochloride, 166.2g of veratraldehyde, 73.3g of nitromethane and 900ml of ethanol into a 2L three-necked flask, stir and dissolve, add 8.03g of diethylamine dropwise, and condense with stirring at room temperature. During the reaction, solid Gradually precipitate out. After the reaction, filter with suction, wash the filter cake with a small amount of cold ethanol, and dry under vacuum at 40°C to obtain 187.0 g of light yellow solid 3,4-dimethoxy-β-nitrostyrene, with a yield of 89.4%.

[0059] 2. Synthesis of 3,4-dimethoxyphenethylamine

[0060] Add 187.0g of 3,4-dimethoxy-β-nitrostyrene, 8.0g of 10% palladium carbon, 400g of hydrazine hydrate, and 900ml of methanol into a 3L three-necked flask, protect with nitrogen, stir, and heat up to 60-65°C for reaction 6~8h. After the reaction was complete, the pH...

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Abstract

The invention provides a method which comprises the following steps: taking veratraldehyde as a starting raw material, firstly carrying out condensation reaction with nitromethane to generate 3, 4-dimethoxy-beta-nitrostyrolene, carrying out catalytic reduction to obtain 3, 4-dimethoxy phenylethylamine, carrying out reaction with hydrobromic acid to remove methoxy, and finally salifying with hydrochloric acid to obtain dopamine hydrochloride. The preparation method has the advantages of cheap and easily available initial raw materials, simple process, no high-temperature and high-pressure steps, low cost, high purity and high yield, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, in particular to a preparation method of dopamine hydrochloride. Background technique [0002] Dopamine hydrochloride, the English name is Dopamine Hydrochloride, and the chemical name is 4-(2-aminoethyl)-1,2-benzenediol hydrochloride. Dopamine hydrochloride is a dopamine receptor agonist, suitable for shock syndrome caused by myocardial infarction, trauma, endotoxin sepsis, cardiac surgery, renal failure, congestive heart failure, etc. Especially in shock with oliguria and normal or low peripheral vascular resistance. Since this product can increase cardiac output, it is also used for cardiac insufficiency where digitalis and diuretics are ineffective. [0003] Dopamine was first synthesized in 1910 by George Barger and James Ewens at the Wellcome Laboratory in London, England. Subsequently, also in the Wellcome laboratory, Henry Dale discovered that it is a weak sympathomimetic, ...

Claims

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Application Information

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IPC IPC(8): C07C213/00C07C215/52C07C213/02C07C217/60C07C201/12C07C205/32
CPCC07C201/12C07C213/02C07C213/00C07C205/32C07C217/60C07C215/52
Inventor 盛遵田郭恒邓义蒙刘发文李广乾王海峰尹凤学丁凤娟杨荣
Owner 山东达冠医药科技有限公司
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