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Preparation process of amantadine hydrochloride

A technology of amantadine hydrochloride and preparation process, applied in the field of preparation technology of amantadine hydrochloride, can solve the problem that amantadine has no resistance to influenza B virus and parainfluenza virus, etc., so as to improve product purity and improve product yield Effect

Inactive Publication Date: 2017-12-08
SHANDONG HOLLY PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Clinically, amantadine has no anti-influenza B virus and parainfluenza virus effect

Method used

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  • Preparation process of amantadine hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Preparation process of amantadine hydrochloride

[0045] (1) Add 400mL of 25% oleum to a 1000mL three-necked reaction flask, stir and cool to 10°C, add 100g of adamantane, control the temperature in the reaction flask at 10°C, and slowly add dropwise at a rate of 0.1mL / s After dropping 80 mL of acetonitrile, the temperature of the solution in the reaction flask was raised to 15°C for 2h, then to 25°C for 2h, and finally to 32°C for 1h, the reaction was completed.

[0046] (2) Add 2000 mL of water to another 3000 mL three-necked reaction flask, stir and cool down to 5°C, slowly add the reaction solution of step (1) at a rate of 2 mL / s, and control the dropping temperature at about 5°C. After finishing, control the temperature of the solution to keep at about 5°C, while stirring for 0.5h, filter, and drain to obtain 1-acetamide fundmantane.

[0047] (3) Add 800 mL of 30% industrial hydrochloric acid to a 1000 mL three-necked reaction flask, and then add the 1-acetamide methaned...

Embodiment 2

[0049] The main difference from Example 1 lies in the difference in the process of raising the temperature in the first step, which is specifically as follows.

[0050] (1) Add 400mL of 25% oleum to a 1000mL three-necked reaction flask, stir and cool to 10°C, add 100g of adamantane, control the temperature in the reaction flask at 10°C, and slowly add dropwise at a rate of 0.1mL / s After dropping 80 mL of acetonitrile, the temperature of the solution in the reaction flask was raised to 20°C for 1 hour, then to 30°C for 1 hour, and finally to 35°C for 2 hours. The reaction was completed.

[0051] (2) Add 2000 mL of water to another 3000 mL three-necked reaction flask, stir and cool down to 5°C, slowly add the reaction solution of step (1) at a rate of 2 mL / s, and control the dropping temperature at about 5°C. After finishing, control the temperature of the solution to keep at about 5°C, while stirring for 0.5h, filter, and drain to obtain 1-acetamide fundmantane.

[0052] (3) Add 800 ...

Embodiment 3

[0054] The main difference from Example 1 lies in the difference in the process of raising the temperature in the first step, which is specifically as follows.

[0055] (1) Add 400mL of 25% oleum to a 1000mL three-necked reaction flask, stir and cool to 10°C, add 100g of adamantane, control the temperature in the reaction flask at 10°C, and slowly add dropwise at a rate of 0.1mL / s After dropping 80 mL of acetonitrile, the temperature of the solution in the reaction flask was increased to 18°C ​​for 1.5h, then to 30°C for 1h, and finally to 35°C for 1.5h, and the reaction was completed.

[0056] (2) Add 2000 mL of water to another 3000 mL three-necked reaction flask, stir and cool down to 5°C, slowly add the reaction solution of step (1) at a rate of 2 mL / s, and control the dropping temperature at about 5°C. After finishing, control the temperature of the solution to keep at about 5°C, while stirring for 0.5h, filter, and drain to obtain 1-acetamide fundmantane.

[0057] (3) Add 800 ...

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Abstract

The invention provides a preparation process of amantadine hydrochloride. The preparation process comprises the following steps: A, adding fuming sulfuric acid into a reactor, cooling to 8 to 10 DEG C, adding adamantine, dropwise adding acetonitrile at the speed of 0.1 to 0.2 mL / s, heating the solution in the reactor to 15 to 20 DEG C and preserving heat for 1 to 2 hours, then heating to 25 to 30 DEG C and preserving heating for 1 to 2 hours, AND finally heating to 32 to 35 DEG C and preserving heating for 1 to 2 hours to complete the reaction; B, carrying out a hydrolysis reaction of the reaction liquid after the reaction in the step A in water, and separating out 1-acetamidoadamantane; C, carrying out a hydrolysis reaction of the 1-acetamidoadamantane in hydrochloric acid, cooling and separating out the amantadine hydrochloride. By the preparation process, the generation of side reaction is reduced by the modes of heating by stages, adding the raw materials slowly and dropwise, mixing at low temperature and the like, and the yield of the amantadine hydrochloride is increased.

Description

Technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation process of amantadine hydrochloride. Background technique [0002] Amantadine is the first antiviral drug approved in the United States. Davis first discovered its antiviral effect in 1964, and it was successively included in the British Pharmacopoeia, American Pharmacopoeia, Japanese Pharmacopoeia and Chinese Pharmacopoeia. Domestic production started in 1971. [0003] Amantadine has antiviral properties. It can be used orally to treat and prevent influenza A and treat Parkinson's neurological disorders. It can also be used to treat zoster and neuralgia after zoster. At present, amantadine has been widely used in anti-influenza, and it is believed that amantadine administration within 48 hours of onset can alleviate the symptoms of influenza A virus. Abroad, amantadine is used to prevent and treat influenza. The main dosage forms are single tablets, capsules and amantad...

Claims

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Application Information

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IPC IPC(8): C07C211/38C07C209/62C07C209/84C07C233/06C07C231/06
CPCC07C209/62C07C209/84C07C231/06C07C233/06C07C211/38
Inventor 李兰花裘月南吴华强蔺珍
Owner SHANDONG HOLLY PHARM CO LTD
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