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

Participants

Reaction Steps

A slurry of 10% Pd/C (0.500 g) in EtOAc (10 mL) was added to a solution of tert-butyl 4-(4-nitrophenyl)piperazine-1-carboxylate (I4) (3.24 g, 10.5 mmol) in EtOAc (90 mL) and the resulting suspension was stirred under a hydrogen atmosphere for 42 hours at room temperature. The catalyst was removed by filtration through Celite, washing with EtOAc (7×10 mL), then the filtrate was evaporated to dryness to give the title compound K3 as a pale pink solid (2.92 g, 99%); 1H NMR (400 MHz, d6-DMSO) δ 6.72-6.66 (m, 2H), 6.52-6.45 (m, 2H), 4.60 (s, 2H), 3.44-3.39 (m, 4H), 2.87-2.79 (m, 4H), 1.41 (s, 9H). LCMS-A: rt 4.40 min; m/z 278.2 [M+H]+.

Provenance & Evidence