Triethylamine → 2-Phenoxy-N-[3-(4-piperidinyl) phenyl]nicotinamide

Participants

Reaction Steps

A mixture of tert-butyl 4-[3-(amino)phenyl]-1-piperidinecarboxylate (0.15 mmol), 2-phenoxynicotinoyl chloride (0.23 mmol) and triethylamine (0.30 mmol) in 3 mL of solvent (CH2Cl2:THF, 1:3) was stirred at room temperature for 12 hours. The reaction mixture was purified by preparative TLC (silica, EtOAc:hexane 1:1) to afford the desired product, tert-butyl 4-(3-{[(2-phenoxy-3-pyridinyl)carbonyl]amino}phenyl)-1-piperidinecarboxylate. Trifluoroacetic acid (1.0 mL) was added to the purified product dissolved in 1.0 mL of CH2Cl2 and the solution was stirred at room temperature for 1 minute. The reaction mixture was concentrated in vacuo to afford the TFA salt of the desired product. 1H NMR (400 MHz, CDCl3) δ 9.85 (s, 1H), 8.76-8.64 (br, 1H), 8.30-8.14 (br, 1H), 7.67 (s, 1H), 7.49 (t, 2H, J=7.8 Hz), 7.42-7.29 (m, 3H), 7.24 (t, 3H, J=5.2 Hz), 7.03 (d, 1H, J=7.2 Hz), 3.59 (bd, 2H, J=11.5), 3.16-3.02 (m, 2H), 2.9-2.79 (m, 1H), 2.14-2.01 (m, 4H); ESIMS m/e: 374.1 [M+H]+.

Provenance & Evidence