Benzylamine → Benzenemethanamine, N-[6-(3-butynyloxy)hexyl]-

Participants

Reaction Steps

A mixture of 6-bromohexyl but-3-ynyl ether (21.5 g) and benzylamine (49.3 g) was heated at 120° for 2 h. The mixture was cooled and partitioned between 2M hydrochloric acid (40 ml) and ethyl acetate (2×200 ml). The combined extracts were washed with an aqueous sodium bicarbonate solution (100 ml), water (200 ml) and dried (Na2SO4). The solvent was removed in vacuo and the residue was purified by chromatography (Merck 9385) eluting with 2% methanol/chloroform. The appropriate fractions were evaporated to give the title compound (25.3 g). LCMS RT=2.2 min.

Provenance & Evidence