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Preparation method of 2-aminoindan

A technology for aminoindane and indoxime, which is applied in the field of organic chemical synthesis, can solve the problems of no industrial practical value, high requirements on reaction vessels, unfavorable industrial production, etc., and achieves the effects of low cost, good product appearance, and few reaction steps.

Inactive Publication Date: 2015-05-20
XUCHANG HAOFENG CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the first method has no industrial practical value because the yield is too low and the reproducibility is poor; while the second method makes the cost too high due to the need to use expensive transition metal catalysts such as palladium on the one hand, and the pressure on the other hand The hydrogenation reduction reaction is a special reaction, which has high requirements on the reaction vessel and requires special operations, which has great potential safety hazards and is very unfavorable for industrial production.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] At room temperature, 147 g of 2-indene oxime, 54 g of potassium borohydride, 150 g of aluminum trichloride and 1000 mL of tetrahydrofuran were successively added into a 3000 mL three-necked flask. After the addition, the temperature was raised to 70 degrees Celsius and refluxed and stirred for 6 hours. Cool after the reaction, and recover the solvent by suction filtration, add 30mL10% sodium hydroxide aqueous solution to the filter cake, heat and reflux for 1 hour, cool to room temperature, extract with 6×100mL chloroform, combine the organic phases and dry with anhydrous sodium sulfate , The solvent was distilled off under reduced pressure, and the residue was rectified under reduced pressure to obtain 87 grams of brown transparent liquid product 2-aminoindan. Normalized purity by gas chromatography: 99.5%.

[0023] NMR: [1H-NMR(CDCl 3 , 400MHz) δ: 2.94-2.98 (m, 2H), 3.24-3.30 (m, 3H), 5.20-5.28 (ws, 2H), 7.20-7.24 (m, 4H).

[0024] Low resolution mass spectrum: LRMS...

Embodiment 2

[0026] Add 147g of 2-indene oxime, 54g of potassium borohydride, 1000mL of tetrahydrofuran and 100g of sulfuric acid to a 3000mL three-necked flask in an ice bath. After the addition, the temperature was raised to 70°C and refluxed for 2 hours with stirring. After cooling, 30 mL of hydrochloric acid was added, and after stirring for half an hour, the solvent was recovered by suction filtration. Add 100mL of 10% sodium hydroxide aqueous solution to the filter cake for neutralization and extract with 6×100mL of chloroform, combine the organic phases and dry with anhydrous sodium sulfate, evaporate the solvent under reduced pressure, and obtain 82 gram of the product 2-aminoindan as a brown transparent liquid. Normalized purity by gas chromatography: 99.6%.

[0027] NMR and low-resolution mass spectrometry information is consistent with Example 1.

Embodiment 3

[0029] Add 147g of 2-indene oxime, 54g of potassium borohydride, 1000mL of tetrahydrofuran and 130mL of boron trifluoride diethyl etherate in a 3000mL three-necked flask successively under ice-cooling. After cooling, 30 mL of hydrochloric acid was added, and after stirring for half an hour, the solvent was recovered by filtration. Add 100mL of 10% sodium hydroxide aqueous solution to the solid filtrate for neutralization, then extract with 6×100mL chloroform, combine the organic phases and dry them with anhydrous sodium carbonate, evaporate the solvent under reduced pressure, and rectify the residue under reduced pressure 94 g of the product 2-aminoindan were obtained as a brown transparent liquid. Normalized purity by gas chromatography: 99.5%.

[0030] NMR and low-resolution mass spectrometry information is consistent with Example 1.

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Abstract

The invention provides a preparation method of 2-aminoindan. Under the catalytic effect of lewis acid such as lithium chloride, aluminium chloride and magnesium chloride, 2-indene oxime is reduced by using potassium borohydride to prepare 2-aminoindan. The synthesis method disclosed by the invention can be completed in one step and has the advantages of less reaction steps, convenient operation, simple separation and purification method and operation, high yield and low cost; the product has good appearance, good color and luster and high purity (99.5%); in addition, the reducing agent used in the method is low in price and easily available; therefore, the preparation method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, in particular to a preparation method of a pharmaceutical intermediate, in particular to a preparation method of 2-aminoindane. Background technique [0002] 2-Aminoindan is an important pharmaceutical intermediate, which can be used in the synthesis of various drugs. For example, the antihypertensive drug delapril and the antiarrhythmic drug ambrodin are all used in the preparation of 2-aminoindan. [0003] At present, the synthetic method of 2-aminoindane mainly contains: 1. take indene as raw material, after it is added with tert-butyl chlorocarbamate, obtain product 2-aminoindane through reductive dechlorination; 2. use 2 -indene oxime as raw material, the product 2-aminoindane is obtained by high-pressure hydrogenation reduction. [0004] However, the first method has no industrial practical value because the yield is too low and the reproducibility is poor; while the second metho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/40C07C211/42
Inventor 刘成张满良孙光辉邢远骆俊陈震宇杨廷飞王豪征陶韬张佩云
Owner XUCHANG HAOFENG CHEM TECH
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