2-Nitrobenzenesulfonyl chloride → HCID 69119040, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydrogen carbonate (21.7 g) and acetone (50 ml) was added to a solution of (S)-(+)-2-methylpiperazine (6.0 g) in water (75 ml). The resulting suspension was cooled (0-5° C.) and a solution of 2-nitrobenzenesulphonyl chloride (15.9 g) in acetone (25 ml) was added, the reaction mixture was allowed to stir at ambient temperature overnight. Water (60 ml) was added and volatile material was removed by evaporation. The residue was acidified to pH 2 by the addition of HCl (2 M, 75 ml) and the mixture was extracted into DCM (2×100 ml). The aqueous phase was adjusted to pH 10-11 by the addition of NaOH (2 M, 50 ml) and extracted into EtOAc (2×150 ml). The organic washings were combined, dried and concentrated to leave the title compound (14.1 g) as a yellow oil. NMR: 1.06 (d, 3H), 2.35-2.43 (m,1H), 2.73-3.06 (m, 4H), 3.65-3.71 (m, 2H), 7.59-7.62 (m, 1H), 7.68-7.72 (m, 2H), 7.95-7.98 (m, 1H); m/z (+ve ESP): 286 (M+H)+.

Provenance & Evidence