1-(4-Bromo-3-nitrophenyl)-4-methylpiperazine → 2-Bromo-5-(4-methylpiperazin-1-yl)phenylamine

Participants

Reaction Steps

A suspension of iron powder (1.77 g, 31.6 mmol) in saturated aqueous ammonium chloride solution (140 ml) at 100° C., was treated dropwise with a solution of 1-(4-bromo-3-nitrophenyl)-4-methylpiperazine (D26) (3.54 g, 11.8 mmol) in methanol (70 ml). The mixture was refluxed for a further 1 h, and was then cooled and partitioned between water and 3% methanol in dichloromethane. The organic phase was dried (Na2SO4) and evaporated under reduced pressure to give the crude product. This was purified by chromatography on silica gel, eluting with methanol and dichloromethane to give the title compound (D27) as a white solid (2.18 g, 68%) MH+=270/272.

Provenance & Evidence