Ammonia → 3-p-biphenylyl-butylamine. Hydrochloride

Participants

Reaction Steps

A solution of 23.9 g of 3-p-biphenylyl-butyramide [m.p. 156°-158°' obtainable by Friedel-Crafts acetylation of biphenyl to give 4-acetylbiphenyl (m.p. 118°-120°), reaction with bromoacetic acid ethyl ester/zinc to give 3-p-biphenylyl-3-hydroxy-butyric acid ethyl ester (m.p. 55°-56°), treatment with HI/acetic acid, reaction of the resulting 3-p-biphenylyl-butyric acid (m.p. 118°-12-°) with SOCl2 to give the chloride, and reaction with ammonia] in 500 ml of THF is added dropwise, while stirring, to a suspension of 7.6 g of LiAlH4 in 250 ml of absolute THF, the mixture is boiled for 16 hours, ethyl acetate is added, with cooling, followed by 32% sodium hydroxide solution and the mixture is worked up in the customary manner to give 3-p-biphenylyl-butylamine. Hydrochloride, m.p. 226° 228°.

Provenance & Evidence