5-(Dimethylamino)pentanenitrile → 5-(Dimethylamino)amylamine

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) solution of lithium aluminum hydride (8 ml, 0.5M in ether) is added, slowly, a solution of 5-(dimethylamino)-pentanenitrile (126 mg, 1 mmol, reference example 94a) in ether (1 mL). On complete addition, the cold bath is removed and stirring continued for 2 h. The reaction mixture is then cooled to 0° C. and quenched by dropwise addition of water (160 mL), sodium hydroxide solution (160 mL, 5M), then a further portion of water (160 mL). The resulting mixture is filtered through celite and the filtrate concentrated under reduced pressure to give an oil which is used without further purification.

Provenance & Evidence