Tert-butyl 4-(2-cyanophenyl)piperazine-1-carboxylate → Tert-butyl 4-[2-(aminomethyl)phenyl]piperazine-1-carboxylate

Participants

Reaction Steps

Platinum oxide (200 mg) was added to a solution of 2-[4-(t-butoxycarbonyl)piperazin-1-yl]benzonitrile (2.01 g, 7 mmol) in ethanol-acetic acid (95:5, 35 mL) and the mixture was shaken under hydrogen (50 psi) for 22 h, adding further platinum oxide (1 g) after 4 h. The mixture was filtered through Hyflo, further ethanol (85 mL), acetic acid (15 mL) and platinum oxide (1 g) were added and the mixture was shaken under hydrogen (50 psi) for 6 h., adding further platinum oxide (200 mg) after 2 h. and 4 h. The mixture was filtered through Hyflo and the solvent was evaporated under reduced pressure. Water (50 mL) was added, the pH was adjusted to 10.0 with aqueous potassium carbonate (saturated) and the mixture was extracted with ether (3×50 mL). The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure to give the crude title compound as a pale yellow oil (2.03 g, 100%), δH (360 MHz, CDCl3) 7.34-7.08 (4H, m), 3.91 (2H, s), 3.57 (4H, t, J 4.9 Hz), 2.87 (4H, t, J 4.9 Hz), 1.60 (2H, br s), and 1.49 (9H, s).

Provenance & Evidence