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Synthetic method for rimantadine

A technology of rimantadine and its synthesis method, which is applied in the preparation of amino-substituting functional groups, organic chemistry, etc., can solve the problems of high cost and high cost, and achieve the effects of low synthesis cost, high yield and cheap raw materials

Inactive Publication Date: 2015-05-13
ANHUI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The expensive Raney-Ni catalyst that this method uses in reaction, cost is too high (the synthesis of rimantadine hydrochloride, Chinese Journal of Pharmaceutical Industry, 2008,39 (10))

Method used

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  • Synthetic method for rimantadine

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Effect test

Embodiment 1

[0028] The present embodiment prepares rimantadine according to the following steps:

[0029] (1) Preparation of 1-bromoadamantane:

[0030] Add 5g of adamantane and 4mL of liquid bromine in sequence in the flask, heat to 85°C for 6h, then heat in an oil bath at 113°C for 3h, let stand for 10h, distill off excess liquid bromine, and then use 3mL of saturated sodium bisulfite to reduce the reaction The remaining liquid bromine in the liquid was filtered, the filter cake was washed to neutrality, dried at 100°C for 3 hours, and recrystallized by methanol to obtain 7.2 g of light yellow crystals, namely 1-bromoadamantane, with a yield of 92.4%.

[0031] (2) Preparation of adamantanecarboxylic acid:

[0032] Add 2g of 1-bromoadamantane, 20mL of anhydrous ether, excess magnesium powder and 0.1g of iodine into a 50mL three-necked flask, replace with nitrogen 3 times, react for 2h, until the magnesium powder does not decrease, and pass CO into the reaction solution 2 At the end of ...

Embodiment 2

[0040] The present embodiment prepares rimantadine according to the following steps:

[0041] (1) Preparation of 1-bromoadamantane:

[0042] Add 3g of adamantane and 3mL of liquid bromine successively into a 50mL three-necked flask, heat to 85°C for 6h, then heat in an oil bath at 113°C for 3h, let it stand for 10h, distill off the remaining liquid bromine, and then use 3mL of saturated Sodium bisulfate reduced the remaining liquid bromine in the reaction solution, filtered, washed the filter cake to neutrality, dried at 100°C for 3 hours, and recrystallized through methanol to obtain 4.30 g of light yellow crystals, namely 1-bromoadamantane, with a yield of 92.0% .

[0043] (2) Preparation of adamantanecarboxylic acid:

[0044] Add 4g of 1-bromoadamantane, 40ml of anhydrous ether, excess magnesium powder and 0.2g of iodine into a 50mL three-necked flask, replace with nitrogen 3 times, react for 2h until the magnesium powder does not decrease, and pass CO into the reaction s...

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Abstract

The invention discloses a synthetic method for rimantadine. The synthetic method is characterized by comprising the following steps: firstly, obtaining 1-bromoadamantane by reacting adamantine with liquid bromine; then, acidifying to obtain adamantanecarboxylic acid after reacting 1-bromoadamantane with magnesium and anhydrous ether; obtaining adamantine carbonyl chloride by performing reflux reaction on tehadamantanecarboxylic acid with thionyl chloride; obtaining adamantane methyl ketone by reacting the adamantine carbonyl chloride with (CH3)2CdCu; and finally, obtaining the rimantadine by hydriding and reacting adamantane methyl ketone with hydrochloric acid and ammonia water in the presence of sodium borohydride. The synthetic method disclosed by the invention is gentle in condition, simple in follow-up processing, high in yield, cheap in raw material and low in synthesis cost.

Description

technical field [0001] The invention relates to a synthesis method of rimantadine, which is clinically used for preventing and treating type A influenza virus infection, and can also be used for treating sudden severe pain and measles. Background technique [0002] Rimantadine hydrochloride is an amino derivative of saturated tricyclodecane, the chemical name is α-methyltricyclo[3.3.1.1]decane-1-methylamine hydrochloride, Bristol.Myers Squibb, USA It was developed by the company and first launched in France in 1987. In 1993, it was approved by the U.S. FDA for the prevention and treatment of influenza A virus infection. The clinical efficacy is better than that of amantadine. Such compounds have antiviral effects. The mechanism of action of rimantadine is to change the surface charge of the host cell, inhibit the process of the virus penetrating into sensitive cells and releasing nucleic acid, and inhibit the proliferation of the virus. Riantadine can also be used to treat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/19C07C209/08
Inventor 李广学赵海华段艳文董安周彭飞马钊任少阳
Owner ANHUI UNIV OF SCI & TECH
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