Propargyl bromide → HCID 22416821, compound

Participants

Reaction Steps

A stirred solution of 1-phenyl-2-(4-chlorophenyl)ethylamine (6.00 gm, 2.6×10-2 mol), propargyl bromide (80% in toluene, 4.82 gm, 3.2×10-2 mol), and diisopropylethylamine (5.04 gm, 3.9×10-2 mol) in 50 ml of anhydrous tetrahydrofuran was refluxed at 90° C. under a dry nitrogen atmosphere for four hours. Then, an additional portion of propargyl bromide (0.48 gm, 3.9×10-3 mol) was added, and reflux was continued to another two hours. The reaction mixture was cooled to room temperature, and the resulting white precipitate was removed by filtration. The mother liquor was concentrated on a rotary evaporator, the residue was diluted with 100 ml of diethyl ether, and the resulting white precipitate was again removed by filtration. The etheral mother liquor was quickly extracted with two 50 ml portions of 2N aqueous HCl. Upon standing, the combined aqueous layers yielded the desired intermediate, N-propargyl-1-phenyl-2-(4-chlorophenyl)ethylamine hydrochloride, as an off-white precipitate, which was washed with diethyl ether (4.53 gm, 57%), mp=191°-193°.

Provenance & Evidence