4-Bromobenzoyl chloride → HCID 18357121, compound

Participants

Reaction Steps

A solution of 1-(4-pyridyl)piperazine (0.49 g) in dry dichloromethane (20 ml) and triethylamine (0.7 ml) was treated slowly with a solution of 4-bromobenzoyl chloride (0.7 g) in dry dichloromethane (10 ml). The reaction mixture was then stirred under argon for 2 hours. The dichloromethane solvent was removed by evaporation and the residue dissolved in ethyl acetate. The organic extracts were then washed with aqueous sodium hydrogen carbonate solution, water, brine, dried (Na2SO4) and evaporated to yield a colourless oil. The residual oil was then triturated with diethyl ether and recrystallised from ethyl acetate/isohexane to give 1-(4-pyridyl)-4-(4-bromobenzoyl)piperazine (0.62 g) as a solid, m.p. 128-129° C.; microanalysis, found: C, 55.7; H, 4.7; N, 12.0%; C16H16N3OBr requires: C, 55.5; H, 4.7; N, 12.1%; NMR: (CDCl3) 3.36(s,4H), 3.73(s,4H), 6.67(dd,2H), 7.33(dd,2H), 7.58(dd,2H), 8.34(dd,2H); MS: m/z 346 (MH)+.

Provenance & Evidence