Cyclopropanecarbonyl chloride → Tert-butyl 4-{3-[(cyclopropylcarbonyl)amino)phenyl}-1-piperidinecarboxylate

Participants

Reaction Steps

According to the procedure used for the synthesis of tert-butyl 4-[3-(propionylamino)phenyl]-1-piperidinecarboxylate, tert-butyl 4-(3-aminophenyl)-1-piperidinecarboxylate (16.47 g 0.0596 mol) and cyclopropanecarbonyl chloride (6.27 g, 0.0597 mol) provided the tert-butyl 4-{3-[(cyclopropylcarbonyl)amino]phenyl}-1-piperidinecarboxylate (18.1 g, 100%). 1H NMR (400 MHz, CDCl3) δ 7.55–7.46 (m, 2H), 7.29–7.21 (m, 2H), 6.96–6.89 (m, 1H), 2.79 (t, 2H, J=12.1 Hz), 2.68–2.58 (m, 1H) 1.84 (d, 2H, J=12.6 Hz), 1.83–1.76 (m, 4H), 1.48 (s, 9H), 1.19–1.12 (m, 1H), 1.09–1.05 (m, 2H), 0.89–0.75 (m, 2H); ESMS m/e: 345.5 (M+H)+.

Provenance & Evidence