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Nitrile reducing process to prepare amine

A technology based on primary amines and hydrocarbon groups, which is applied in the field of reducing nitriles to prepare amines, achieving the effects of low cost, fast speed and low pollution

Inactive Publication Date: 2008-07-23
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Raney nickel is a classic catalyst for catalytic hydrogenation, but in recent years there have also been non-hydrogen sources of hydrogen such as: Shankare Gowda etc. have obtained more than 70% yields with Raney nickel and hydrazine formic acid reduction of nitrile (see Shankare Gowda and D. Channe Gowda Tetrahedron 2002, 58, 2211-2213), however the toxicity of hydrazine and the moderate yield are the drawbacks of this method

Method used

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Effect test

Embodiment 1

[0015] Embodiment 1: This embodiment prepares phenylethylamine, raw material is benzyl nitrile:

[0016] Add 5-80mmol KBH to the round bottom flask 4 , put a magnetic stirring bar, add 0-80mL water, carefully add 1-80mmol Raney nickel, then add 5-80mL ethanol and 1.16mL (10mmol) phenylacetonitrile, and stir at -15~70°C. After 45 minutes, the Raney nickel was filtered off, and the filtrate was evaporated to remove ethanol with a rotary evaporator, and 50 mL of ethyl acetate was added to dissolve the product, transferred to a 125 mL separating funnel, washed with water for 3 to 4 times, and the organic phase was transferred to a 100 mL round bottom flask. Add anhydrous Na 2 SO 4 Dry overnight, filter off the desiccant, evaporate ethyl acetate with a rotary evaporator, and use aluminum oxide column chromatography (developing solvent is dichloromethane: methanol 20: 1) to obtain light yellow liquid phenethylamine. 92%.

Embodiment 2

[0017] Embodiment 2: This embodiment prepares p-methoxyphenethylamine, raw material is p-methoxyphenylacetonitrile

[0018] Add 5-80mmol KBH to the round bottom flask 4 , put a magnetic stirring bar, add 0-80mL water, carefully add 1-80mmol Raney nickel, then add 5-80mL ethanol and 1.36mL (10mmol) p-methoxyphenylacetonitrile, and stir at -15~70°C. After 45 minutes, the Raney nickel was filtered off, and the filtrate was evaporated to remove ethanol with a rotary evaporator, and 50 mL of ethyl acetate was added to dissolve the product, transferred to a 125 mL separating funnel, washed with water for 3 to 4 times, and the organic phase was transferred to a 100 mL round bottom flask. Add anhydrous Na 2 SO 4 Dry overnight, filter off the desiccant, evaporate ethyl acetate with a rotary evaporator, and use aluminum oxide column chromatography (developing solvent is dichloromethane:methanol 20:1) to obtain a colorless liquid p-methoxyphenethyl Amine, 86% yield.

Embodiment 3

[0019] Embodiment 3: This embodiment prepares p-chlorophenethylamine, raw material is p-chlorophenylacetonitrile

[0020] Add 5-80mmol KBH to the round bottom flask 4 , put a magnetic stirring bar, add 0-80mL water, carefully add 1-80mmol Raney nickel, then add 5-80mL ethanol and 1.51g (10mmol) p-chlorophenylacetonitrile, and stir at -15~70°C. After 45 minutes, the Raney nickel was filtered off, and the filtrate was evaporated to remove ethanol with a rotary evaporator, and 50 mL of ethyl acetate was added to dissolve the product, transferred to a 125 mL separating funnel, washed with water for 3 to 4 times, and the organic phase was transferred to a 100 mL round bottom flask. Add anhydrous Na 2 SO 4 Dry overnight, filter off the desiccant, evaporate ethyl acetate with a rotary evaporator, and use aluminum oxide column chromatography (developing solvent is dichloromethane:methanol 20:1) to obtain a colorless liquid p-methoxyphenethyl Amine, 90% yield.

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Abstract

The present invention is reduction process of nitrile to prepare amine. By using potassium borohydride as reductant and Raney nickel as catalyst, nitrile may be reduced effectively into corresponding primary amine. By means of regulating the activity of the reduction system, 2-(1-hydroxy cyclohexyl)-2-(4-methoxy phenyl) acetonitrile may be reduced into 1-(2-amino-1-(4-methoxy phenyl) cyclohexanol as the intermediate for preparing phenylethyl amine antidepressant venlafaxine. By using potassium borohydride as reductant, the present invention has low cost, high safety, mild reaction condition at normal pressure, no need of N2 protection, primary amine yield over 80 %, less pollution and other advantages.

Description

technical field [0001] The invention relates to a method for preparing amines by reducing nitriles. Background technique [0002] Amines are widely used as solvents, pesticides and pharmaceuticals, and the reduction of nitriles is a very important and commonly used method for the preparation of amines. However, the reduction of nitriles to amines will go through the imine stage, which is easy to form coupling products (secondary amines). Therefore, the selective reduction of nitriles to primary amines has become a hot spot in recent years. The method is usually to use lithium aluminum hydride or catalytic hydrogenation (see (1) Walker.E.R.H.Chem.Soc.Rev.1976,5,23-50; 66, 2480-2483.) The reduction of nitriles by catalytic hydrogenation usually requires high temperature and high pressure. The main limitation of lithium aluminum hydride is that it decomposes and spontaneously ignites when it meets moisture, which is easy to cause fire, and the industrial production is danger...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/48C07C211/00C07C211/01C07C211/43B01J25/02
Inventor 余孝其吴波
Owner SICHUAN UNIV
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