Hydrochloric Acid → HCID 70874117, compound

Participants

Reaction Steps

To a solution of tert-butyl 4-{[5-chloro-3-(methoxycarbonyl)-2-methylphenyl](ethyl)amino}piperidine-1-carboxylate (131 mg, 0.32 mmol) in tetrahydrofuran (2 ml) was added LiOH (8.4 mg, 0.35 mmol) in deionized water (2 ml). The reaction mixture was stirred in air at room temperature for 24 hours. 1M NaOH (3.19 ml) was added to the reaction mixture and this was stirred for a further 24 hours. The reaction mixture was then warmed to 40° C. for 25 h. The reaction mixture was acidified to pH 2-3 with 1M HCl and extracted with EtOAc (3×20 ml). The combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure to give 122 mg of the title compound as a thick orange oil. LC-MS 76%, m/z=397.5/399.4, 1H NMR (500 MHz, Chloroform-d) δ ppm 7.74 (1H, s), 7.20-7.35 (2H, m), 3.92-4.11 (2H, m), 2.97-3.13 (2H, m), 2.81-2.95 (1H, m), 2.62-2.79 (2H, m), 2.53 (3H, s), 1.75 (2H, br. s.), 1.48-1.61 (2H, m), 1.46 (9H, s), 0.89 (3H, t, J=6.86 Hz).

Provenance & Evidence