Preparation method of 3-amino-1-adamantanol

A technology for adamantane alcohol and amantadine amine, which is applied in the field of preparation of 3-amino-1-adamantanyl alcohol, can solve the problems of complicated operation, unsuitable for industrial production and high cost, and achieves simple operation, environmental friendliness and low cost. Effect

Active Publication Date: 2015-07-08
SHANGHAI VIWIT PHARMA CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] The technical problem to be solved by the present invention is to overcome the low yield generally in the preparation method of existing 3-amino-1-adamantanol, raw material is difficult to obtain, expensive, high cost, complicated operation, potential safety hazard and It is not suitable for technical problems such as defects such as industrialized production, but provides a preparation method of 3-amino-1-adamantanol

Method used

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  • Preparation method of 3-amino-1-adamantanol
  • Preparation method of 3-amino-1-adamantanol
  • Preparation method of 3-amino-1-adamantanol

Examples

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Effect test

Embodiment 1

[0043] Preparation of mixed acid: under normal temperature, add 96.9g (1mol) of concentrated nitric acid dropwise into 735.6g (7.5mol) of concentrated sulfuric acid, keeping the temperature not higher than 30°C. In the mixed acid, the molar ratio of concentrated nitric acid to concentrated sulfuric acid is 1:7.5.

[0044] (1) Under normal temperature conditions, 735.6g (7.5mol) concentrated sulfuric acid is added in the reactor, then add 187.7g (1mol) amantadine hydrochloride in batches, stir, until dissolving, amantadine hydrochloride and The molar ratio of concentrated sulfuric acid is 1:7.5. Add the mixed acid dropwise to the reactor, keeping the temperature not higher than 30°C. When 1 / 3 of the amount is added dropwise, stir for about 1 hour, then add the remaining mixed acid dropwise. After the dropwise addition, the amantadine hydrochloride in the reactor The molar ratio of salt to concentrated nitric acid is 1:1. After stirring at room temperature for 16 hours, GC (ga...

Embodiment 2

[0050] Preparation of mixed acid: Add 96.9g (1mol) of concentrated nitric acid dropwise into 441.4g (4.5mol) of concentrated sulfuric acid at room temperature, keeping the temperature not higher than 30°C. In the mixed acid, the molar ratio of concentrated nitric acid to concentrated sulfuric acid is 1:4.5.

[0051] (1) Under normal temperature conditions, add 441.4g (4.5mol) of concentrated sulfuric acid into the reactor, then add 187.7g (1mol) of amantadine hydrochloride in batches, stir to obtain a white turbid liquid, amantadine hydrochloride The molar ratio to concentrated sulfuric acid is 1:4.5. Add the mixed acid dropwise into the reactor and keep the temperature not higher than 30°C. When 1 / 3 of the amount is added dropwise, stir for 1 hour, then add the remaining mixed acid dropwise. After the dropwise addition, amantadine hydrochloride and The molar ratio of concentrated nitric acid is 1:1. After stirring at room temperature for 10 hours, the GC central control sho...

Embodiment 3

[0054] Preparation of mixed acid: Add 126.0g (2.0mol) of fuming nitric acid dropwise into 490.4g (5.0mol) of concentrated sulfuric acid at room temperature, keeping the temperature not higher than 30°C. In the mixed acid, the molar ratio of fuming nitric acid to concentrated sulfuric acid is 1:2.5.

[0055] (1) Under normal temperature conditions, add 490.4g (5.0mol) of concentrated sulfuric acid into the reactor, then add 187.7g (1mol) of amantadine hydrochloride in batches, and stir to obtain a white turbid liquid. The molar ratio of amantadine hydrochloride to concentrated sulfuric acid is 1:5.0. Add the mixed acid dropwise into the reactor and keep the temperature not higher than 30°C. When 1 / 3 of the amount is added dropwise, stir for 1 hour, then add the remaining mixed acid dropwise. After the dropwise addition, the molar ratio of amantadine hydrochloride to concentrated nitric acid in the reactor was 1:2. After stirring at room temperature for 18 hours, the GC contro...

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Abstract

The invention discloses a preparation method of 3-amino-1-adamantanol, which comprises following steps: (1) adding amantadine or a salt thereof to sulfuric acid at 10-30 DEG C and adding dropwisely a mixed acid to perform a nitration reaction to obtain a reaction liquid; (2) adding the reaction liquid to water and mixing the reaction liquid with water to obtain a mixed solution; (3) performing a hydroxylation reaction under the effect of an alkaline to obtain the 3-amino-1-adamantanol . The preparation method employs the raw material being easy to obtain, is simple in operations, is environmental-protective, is low in cost, is high in yield which is generally higher than 80%, maximally 90.1%, and is more suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of 3-amino-1-adamantanol. Background technique [0002] China has become the world's largest diabetes country. At present, there are 382 million diabetic patients in the world, and it is expected to reach 552 million in 2030, an increase of 50.7%. Diabetes patients in China account for a quarter of the world's total, a total of 98 million people, and it is expected to reach 129.7 million in 2030. The diabetes drug market is bound to show a trend of rapid growth, and as a diabetes treatment drug dipeptidyl peptidase Ⅳ (DPP-Ⅳ) inhibitor has occupied a certain market share, and has broken the market share of insulin, sulfonylureas, biguanides and α-glucosidase. The pattern of drugs such as inhibitors. [0003] As a dipeptidyl peptidase Ⅳ (DPP-Ⅳ) inhibitor, vildagliptin was developed by Novartis and was first applied for marketing in 2006. It is currently on the market in many countries in the world. The co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/00C07C215/44
Inventor 魏彦君张保军
Owner SHANGHAI VIWIT PHARMA CO LTD
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