4-Nitrobenzaldehyde → 1-Methyl-4-(4-nitrobenzyl)piperazine

Participants

Reaction Steps

To a 0° C. cooled solution of 4-nitrobenzaldehyde in DCM (40 mL) was added Na(OAc)3BH (10.526 gm, 49.66 mmol) and the reacton was stirred for 10 min. To the reaction mixture was added N-methylpiperazine (9.93 g, 99.3 mmol) under nitrogen atmosphere and the reaction mixture was continued stirring at room temperature for 4 h. The progress of the reaction was monitored by TLC and upon completion of the reaction, the mixture was partitioned between DCM (20 mL) and water (15 mL) and the organic layer was separated, washed with water (2×15 mL), dried over sodium sulphate, filtered and the solvent was removed under reduced pressure to give crude residue. Washing with ether gave 1-methyl-4-(4-nitrobenzyl)piperazine (4 g). 1H NMR (CDCl3, 200 MHz) δ: 8.19 (2H, d, J=8.4 Hz), 7.53 (2H, d, J=8.4 Hz), 3.59 (2H, s), 2.47 (8H, bm), 2.29 (3H, s); m/e=236 (M+1).

Provenance & Evidence