N4-cyclohexylmethyl-2-(4-methyl-piperazin-1-yl)-5-nitro-N1-phenyl-benzene-1,4-diamine → N1-cyclohexylmethyl-5-(4-methyl-piperazin-1-yl)-N4-phenyl-benzene-1,2,4-triamine

Participants

Reaction Steps

To a solution of N4-cyclohexylmethyl-2-(4-methyl-piperazin-1-yl)-5-nitro-N1-phenyl-benzene-1,4-diamine (0.22 g, 0.53 mmol) in THF (5.00 mL) was added 10% palladium on activated carbon (0.22 g). The reaction flask was equipped with a septum and was placed under vacuum for 3 min. This flask was placed under hydrogen atmosphere (balloon inflated with hydrogen) and the reaction mixture was stirred for 18 h. The palladium was filtered off through a plug of diatomaceous earth and washed with EtOAc. The solvent was removed via rotary evaporation. The resulting residue was flash chromatographed (5% MeOH/CH2Cl2), yielding N1-cyclohexylmethyl-5-(4-methyl-piperazin-1-yl)-N4-phenyl-benzene-1,2,4-triamine (0.10 g, 49.5% yield). M+, 392

Provenance & Evidence