1-Boc-4-(4-Nitrobenzyl)piperazine → tert-Butyl 4-((4-aminophenyl)methyl)piperazine-1-carboxylate

Participants

Reaction Steps

tert-Butyl 4-(4-nitrobenzyl)piperazine-1-carboxylate (I92) (0.500 g, 1.56 mmol), ethyl acetate (100 mL) and 10% Pd/C (150 mg) were agitated under a hydrogen atmosphere at 50 psi. After two hours the mixture was filtered through celite and concentrated. The residue was chromatographed (12 g silica cartridge, 0-60% ethyl acetate/petroleum benzine 40-60° C.) to give the title compound (I93) (327 mg, 72% yield) as a white solid; 1H NMR (400 MHz, CDCl3) δ 7.11-7.05 (m, 2H), 6.67-6.61 (m, 2H), 3.62 (s, 2H), 3.43-3.37 (m, 6H), 2.40-2.30 (m, 4H), 1.45 (s, 9H). LCMS Method C: rt 1.80 min; m/z 292.1 [M+H]+.

Provenance & Evidence