4-(4-Chlorophenyl)butanamide → 4-(4-Chlorophenyl)butan-1-amine

Participants

Reaction Steps

To a solution of 12.6 g. (0.33 mole) of lithium aluminum hydride in 340 ml. of dry ether was added dropwise at room temperature 16.4 g. (0.083 mole) of 4-(p-chlorophenyl)-butyramide. The reaction mixture was stirred at room temperature for 4 hours, cooled and cautiously quenched with 13 ml. of water, 10 ml. of 20% sodium hydroxide and 45 ml. of water. The organic layer was separated and the emulsion was extracted with ether. The combined organic and ether extract was dried over sodium hydroxide and concentrated to obtain 4-(p-chlorophenyl)butylamine; m.p. of hydrochloride salt 162°-164° C.

Provenance & Evidence