Ethyl Acetate → HCID 18357133, compound

Participants

Reaction Steps

Carbonyl diimidazole (324 mg) was added to a solution of 6-bromonaphthalene-2-sulphinic acid (658 mg) in dimethylformamide (10 ml). After stirring at ambient temperature for one hour N-4-(4-pyridyl)piperazine (326 mg) was added as a solid in one portion and stirring continued at ambient temperature overnight. The reaction mixture was poured into ethyl acetate (100 ml), washed with water (3×25 ml), brine (25 ml), dried (MgSO4) and evaporated to give a yellow oil which was purified by chromatography on silica gel (Mega Bond Elut column) using an increasing concentration of methanol in dichloromethane (up to 5% methanol) as eluant to give an oil which on trituration with diethyl ether gave a white solid 1-(4-pyridyl)-4-(6-bromonaphtalene-2-sulphenyl)piperazine (170 mg), m.p. 200-202° C.; microanalysis, found: C, 54.9; H, 4.4; N, 10.1; C19H18BrN3OS requires: C, 54.9; H, 4.3; N, 10.1; NMR: 2.9-3.0(m,2H); 3.1-3.3(m,2H); 3.35-3.5(m,4H); 6.8(dd,2H); 7.7-7.8(m,2H); 8.1-8.2(m,4H); 8.3(s,1H); 8.35(d,1H); MS: m/z 416 (MH)+.

Provenance & Evidence