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Simple and novel process for preparing indenes derivatives

A derivative and novel technology, applied in the field of preparation of anti-Parkinson's disease drug rasagiline, which can solve the problems of long synthetic route, reduced overall yield, and increased cost of the final product

Inactive Publication Date: 2007-07-04
北京德众万全医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this method, the synthetic route is relatively long, which easily leads to a reduction in the overall yield and an increase in the cost of the final product.

Method used

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  • Simple and novel process for preparing indenes derivatives
  • Simple and novel process for preparing indenes derivatives
  • Simple and novel process for preparing indenes derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] The synthesis of embodiment 1 1-propargyl indene amine

[0018] Add 130 ml of absolute ethanol to a 250 ml three-necked flask, add 13.2 g of 1-indanone and 6.6 g of propargylamine to it. At 0°C, 3.8 g of sodium borohydride was added in portions. After the addition was completed, the reaction was continued by heating to 45°C, and the reaction was stopped after about 24 hours. Concentrate to remove ethanol, add 130 ml of pure water, extract three times with 130 ml of ethyl acetate, combine the ethyl acetate phases, dry with anhydrous magnesium sulfate, filter with suction, concentrate to remove ethyl acetate to obtain 12.5 g of the target compound.

Embodiment 2

[0019] The synthesis of embodiment 2 1-propargyl indene amines

[0020] Add 100 ml of absolute ethanol to a 250 ml three-necked flask, add 10 g of 1-indanone and 5 g of propargylamine to it. At 0°C, 4 g of sodium borohydride was added in portions. After the addition was completed, the reaction was continued by heating to 45°C, and the reaction was stopped after about 24 hours. Concentrate to remove ethanol, add 100 ml of pure water, extract three times with 100 ml of ethyl acetate, combine the ethyl acetate phases, dry over anhydrous magnesium sulfate, filter with suction, concentrate to remove ethyl acetate to obtain 9.2 g of the target compound.

Embodiment 3

[0021] The synthesis of embodiment 3 1-propargyl indene amines

[0022] Add 150 milliliters of absolute ethanol to the high-pressure reaction tank, add 15 grams of 1-indanone and 7.5 grams of propargylamine, and add 1 g of palladium carbon (5%). Catalytic hydrogenation was carried out at 45°C and 4 atmospheres, and the reaction was stopped after about 24 hours. Remove the catalyst by suction filtration under reduced pressure, concentrate to remove ethanol, add 150 ml of pure water, extract three times with 150 ml of ethyl acetate, combine the ethyl acetate phases, dry with anhydrous magnesium sulfate, filter with suction, and concentrate to remove ethyl acetate to obtain the target compound 13.4 grams.

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Abstract

The invention provides a method for preparing indene derivative. Said compound can be used to prepare Rasagiline that can prevent Parkinson's disease.

Description

field of invention [0001] The invention relates to a preparation method of an indene derivative. The compound can be further used to prepare rasagiline, an anti-Parkinson's disease drug. Background of the invention [0002] Rasagiline (chemical name: R-(+)-N-propargyl-1-aminoindene), has the following formula: [0003] [0004] Rasagiline is a potent, highly selective, irreversible monoamine oxidase (MAO-B) inhibitor that can be used to treat Parkinson's disease. [0005] The publicly reported methods for preparing rasagiline are as follows: [0006] In the world patent WO02068376A1, U.S. patents US5786390 and US5994408, it is introduced to chlorinate indene to obtain 1-chloroindene, and then carry out benzylation by substitution reaction to obtain N-benzyl-1-indenamine, and then to N-benzyl -1-Indenamine racemate is resolved to obtain R-N-benzyl-1-indenamine, catalytic hydrogenation removes the benzyl group to obtain 1-indenamine, and finally reacts with propargyl chlo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/24C07C209/26C07C209/28C07C211/42
Inventor 曲峰
Owner 北京德众万全医药科技有限公司
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