Hydrogen Bromide → HCID 18621546, compound

Participants

Reaction Conditions

Reaction Steps

3-benzyl-1-[2-(4-tert-butoxycarbonylaminophenyl)ethyl]piperidine (0.67 g, 1.69 mmol) was dissolved in HBr (saturated solution in methanol, 10 mL) and the resulting solution stirred at 25° C. for 20 h. Then, after concentration in vacuum, the resultant mixture was treated with NaHCO3 (water saturated solution, 50 mL) and extracted twice with EtOAc (2×50 mL). The collected organic phase was washed with brine (50 mL), dried and concentrated in vacuum. The crude compound was purified by filtration on silica gel using CH2C2/MeOH as eluant to afford the free amine as a pale yellow oil (0.272 g, 55%). 1H NMR (CDCl3): 0.85-1.05 (m, 1H), 1.5-1.9 (m, 4H), 1.9-2.1 (m, 2H), 2.4-2.6 (m, 4H), 2.65-2.8 (m, 2H), 2.85-3.05 (m, 2H), 3.53 (bs, 2H), 6.61 (d, J=8.1 Hz, 2H), 6.97 (d, J=8.1 Hz, 2H), 7.145 (d, J=7.8 Hz, 2H), 7.18 (d, J=7.2, 1H), 7.275 (t, J=7.2 Hz, 2H).

Provenance & Evidence