Sodium Iodide → N-(3-{1-[6-(1H-Indol-1-YL)hexyl]-4-piperidinyl}phenyl)-2-methylpropanamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(6-Chlorohexyl)-1H-indole (23.6 mg, 0.100 mmol), 2-methyl-N-[3-(4-piperidinyl)phenyl]propanamide (24.6 mg, 0.100 mmol), K2CO3 (27.6 mg, 0.200 mmol), NaI (22.5 mg, 0.150 mmol) and DMF (1.00 mL) was heated at 100° C. for 12 h. The reaction mixture was cooled to room temperature and the crude material was purified by preparative TLC using 5% of NH3 (2.0 M in methanol) in CH2Cl2 to give the desired product as a yellow solid (40 mg, 90%): 1H NMR (400 MHz, CDCl3) δ 8.08–6.52 (m, 11H), 4.17 (t, 2H, J=7.2 Hz), 3.26 (d, 2H, J=11.6 Hz), 2.74–2.52 (m, 4H), 2.44–2.28 (m, 2H), 2.20–2.02 (m, 2H), 1.98–1.82 (m, 4H) 1.78–1.62 (m, 2H), 1.43–1.28 (m, 4H), 1.28 (d, 6H, J=6.8 Hz); ESMS m/e: 446.5 (M+H)+.

Provenance & Evidence