A kind of production technology of memantine hydrochloride

A technology of memantine hydrochloride and production process, applied in the field of medicine, can solve problems such as low final yield, and achieve the effects of avoiding the influence of yield, reducing side reactions and improving product yield

Active Publication Date: 2016-05-25
CHENGDU YILUKANG MEDICAL TECH & SERVICE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above method has simple process, little harm to human body, and no pollution to the environment; but the final yield of the above method product is low

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Acetamidolation of 1-bromo-3,5-dimethyladamantane with acetonitrile under the action of concentrated sulfuric acid

[0031] The details are as follows: In a 500ml reaction flask, add 36.5g of 1-bromo-3,5-dimethyladamantane (0.15mol) and 105.75g of acetonitrile, then slowly add 280ml of concentrated sulfuric acid dropwise at a rate of 10-15 drops / minute (97%), stir. Control the reaction temperature at 5°C; stir at room temperature for 12 hours after dropping, then pour the reaction solution into ice water and let it stand for 10 hours, a white precipitate precipitates; filter with suction and dry the filter cake to obtain 1-acetylamino-3, The crude product of 5-dimethyladamantane was 32.49g, and the yield was 97.73%.

Embodiment 2

[0033] 1-Acetamido-3,5-dimethyl hydrolysis under basic conditions to give 1-amino-3,5-dimethyladamantane

[0034] The details are as follows: In a 500ml reaction flask, add 22.1g (0.1mol) of 1-acetylamino-3,5-dimethyladamantane prepared as described in Example 1, 20.1g of ethylene glycol, and 20g of hydrogen Sodium oxide and 55ml of water, slowly warm up and stir to dissolve the sodium hydroxide; control the temperature to 150°C and stir for 12 hours; stop stirring, cool the reaction solution to room temperature and transfer it to ice water, stir well, and let it stand for 1 hour. The oily matter precipitated; repeated extraction with 50ml of petroleum ether for 3 times, combined the petroleum ether layers for 3 times, dried the petroleum ether layer with anhydrous sodium sulfate, and then evaporated the petroleum ether to obtain a light yellow oily liquid which is 1-amino- 3,5-Dimethyladamantane.

Embodiment 3

[0036] 1-amino-3,5-dimethyladamantane was acidified to obtain memantine hydrochloride

[0037] Specifically as follows: get the oil prepared in Example 2, pass through dry hydrogen chloride, white solids are separated out, stop flowing hydrogen chloride gas when the solution pH=6, and the separated white solids are sucked and dried to obtain 19.93 g of memantine hydrochloride crude product, Yield 92.37% (Note: combined with the comprehensive yield of Examples 2 and 3).

[0038] Purification: recrystallized twice with chloroform to obtain 18.84g of the product, with a yield of 87.32% (note: combine the comprehensive yields of Examples 2 and 3).

[0039] For the memantine hydrochloride prepared in the continuous process of the above-mentioned examples 1-3, the comprehensive yield of the final product is 85.33%, which is far higher than the 79% yield of the final product of the memantine hydrochloride prepared in the prior art Chinese patent CN1335299A embodiment 1 . The produc...

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PUM

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Abstract

The invention belongs to the technical field of medicine, in particular to a production process of memantine hydrochloride. The production process of memantine hydrochloride of the present invention comprises the following steps: 1-bromo-3,5-dimethyladamantane reacts with acetonitrile under the action of concentrated sulfuric acid to obtain 1-acetylamino-3,5 -Dimethyladamantane, the temperature of acetylamination reaction is 5-10°C; 1-acetamido-3,5-dimethyl and polyhydric alcohol without ether bond undergo hydrolysis reaction under alkaline conditions to obtain 1-amino-3,5-dimethyladamantane; 1-amino-3,5-dimethyladamantane is acidified with hydrochloric acid and recrystallized to obtain high-purity memantine hydrochloride. The production process of memantine hydrochloride of the present invention is based on the existing synthesis process, by controlling process parameters and changing process conditions, the product yield of memantine hydrochloride is improved.

Description

technical field [0001] The invention belongs to the technical field of medicine, in particular to a production process of memantine hydrochloride. Background technique [0002] Memantine hydrochloride (memantinehydrochloride), also known as 1,3-dimethyl-5-aminoadamantane hydrochloride, memantine hydrochloride, memantine hydrochloride, is a new type of anti-senile dementia drug, first introduced in Germany Merz company researched and developed and sold in Germany in 1984 under the trade name of AkatinolMemantine??, there are conventional tablets, capsules, and oral liquid. And in February 2002 and October 2003, it was approved to go on the market in Europe and the United States. Its chemical name is: 1-amino-3,5-dimethyladamantane hydrochloride, which is a non-competitive, moderately strong and fast voltage-gated N-methyl-D-aspartic acid (NMDA ) receptor antagonist, which can prevent the overload of intracellular calcium and inhibit the excitotoxicity of excitatory amino ac...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/38C07C209/00C07C209/62
Inventor 彭超
Owner CHENGDU YILUKANG MEDICAL TECH & SERVICE
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