2,2-Diphenylacetyl chloride → N-[3-(1-{2-[(Diphenylacetyl)amino]ethyl}-4-piperidinyl)phenyl]-2-methylpropanamide

Participants

Reaction Conditions

Reaction Steps

A mixture of N-{3[1-(2-aminoethyl)-4-piperidinyl]phenyl}-2-methylpropanamide (20.0 mg, 0.0700 mmol), diphenylacetyl chloride (23.0 mg, 0.110 mmol), and TEA (20.0 mg, 0.140 mmol) in THF (2 mL) was stirred overnight at 23° C. The crude product was purified by preparative TLC using CH2Cl2/MeOH/isopropyl amine (19:1:0.2) to give the desired product (8.0 mg, 47%). 1H NMR (400 MHz, CDCl3) δ 7.53 (s, 1H) 7.37–7.20 (m, 13H), 6.97–6.92 (m, 1H) 6.67 (s, 1H) 4.98 (s, 1H), 3.43 (q, 2H, J=5.9 Hz), 2.90 (d, 2H, J=11.6 Hz), 2.57–2.42 (m, 4H), 2.11 (t, 2H, J=10.4 Hz), 1.75 (d, 2H, J=12.4 Hz), 1.70–1.58 (m, 2H), 1.25 (d, 6H, J=6.7 Hz); ESMS m/e: 484.2 (M+H)+.

Provenance & Evidence