N-butyl-4-chlorobenzamide → n-Butyl-4-chlorobenzenemethanamine

Participants

Reaction Steps

A solution of N-butyl-4-chlorobenzamide (2.26 g; 0.011 mol) in dry THF (25 ml) was added slowly to an ice-cooled solution of 1.0M B2H6 --THF complex (45 ml; 0.045 mol) under a nitrogen blanket. When addition was complete, the mixture was stirred and heated to reflux for 3 hours, cooled and decomposed by dropwise addition of 1:1 conc aq HCl-water (10 ml). The mixture was then evaporated on a rotary evaporator at 60° for 1/2 hour to decompose the boron-amine complexes. The residue was taken up in water, strongly basified with aq NaOH and extracted with CH2Cl2 (3×25 ml). The combined extracts were washed with water, dried (MgSO4), filtered and evaporated to give n-butyl-4-chlorobenzenemethanamine (1.79 g) as an oil. The oil was converted to the hydrochloride salt of the title compound (1.98 g) by crystallising from ethanolic HCl and ethyl acetate, mp 250°-252° after melting and resolidifying at 203°-207° .

Provenance & Evidence