Tert-butyl 4-(4-nitrobenzoyl)piperazine-1-carboxylate → Tert-butyl 4-(4-aminobenzoyl)piperazine-1-carboxylate

Participants

Reaction Steps

tert-Butyl 4-(4-nitrobenzoyl)piperazine-1-carboxylate (12.9 g, 38.5 mmol) was dissolved in methanol (150 ml) and transferred into a 500-ml PARR flask. The flask was flushed with nitrogen, 10% Pd/C (0.38 g, 0.357 mmol) was added, flushed again with nitrogen, then hydrogen, then hydrogenate for 17 hours while shaking. (H2 pressure 50 psi). The reaction mixture was filtered through CELITE®, the CELITE® washed with MeOH and the collected liquids concentrated in vacuum. 11.67 g of tert-butyl 4-(4-amino-benzoyl)piperazine-1-carboxylate were isolated as a beige solid. MS (ESI) m/z 306 (M+H). 1H NMR (CDCl3) δ ppm 7.25 (d, 2H, J=7.7), 6.64 (d, 2H, J=7.7), 3.89 (bs, 2H), 3.58 (bs, 4H), 4.43 (bs, 4H), 1.46 (s, 9H).

Provenance & Evidence