Phenylacetonitrile → 2-Amino-3-phenylpropanenitrile

Participants

Reaction Conditions

Reaction Steps

10 millimoles (1.17 g) of benzyl cyanide are dissolved in 0 ml of anhydrous toluene at 0° C., under an argon atmosphere. 15 millimoles of 1.5M toluenic solution of diisobutylaluminum hydride (10 ml) are added, dropwise, at this temperature. The temperature is maintained at 0° C. for one hour, then 13.7 ml (viz 1.5 eq) of diethyl-aluminum cyanide are added. The reaction mixture is stirred for 3 hours while the temperature reaches the room temperature. Then it is hydrolyzed with 10 ml of methanol, and with a slurry of sodium sulfate. After purification of the so-obtained α-aminonitrile, by high pressure liquid chromatrography on silica, with elution by ethyl acetate/petroleum ether, there are obtained 0.95 g of 2-amino -3-phenyl-propionitrile, in the form of an orange-colored oil, yield: 65%.

Provenance & Evidence