Acetonitrile → HCID 24882842, compound

Participants

Reaction Conditions

Reaction Steps

N-[1-(2-Aminoethyl)-piperidin-4-yl]-N-cyclopropyl-3-trifluoromethyl-benzenesulfonamide (114) was prepared as follows. A mixture of compound 19 (0.5 g, 1.4 mmol), compound 113 (160 mg, 1.3 mmol, Aldrich), K2CO3 (1.0 g, 7.2 mmol), KI (10 mg) and benzyltriethylammonium chloride (20 mg, 0.07 mmol, ACROS) in 4 mL of CH3CN was shaken at 60° C. for 24 hours. After cooling to room temperature, the reaction mixture was diluted with EtOAc (20 mL), washed with water (4 mL) and brine (4 mL), concentrated and purified by column (Silica gel, EtOAc/MeOH/NH4OH 100/10/1) to give the title compound 114 as a free base, which was converted to its HCl-salt by treating with 1N HCl and dried (HCl-salt, white solid, yield 30%): 1H NMR (400 MHz, CD3OD, HCl-salt): δ 8.22 (d, 1H, 7.9 Hz), 8.18 (s, 1H), 8.04 (d, 1H, 7.9 Hz), 7.88 (dd, 1H, 7.8 & 7.9 Hz), 4.24-4.31 (m, 1H), 3.69-4.73 (m, 2H), 3.44-3.47 (m, 4H), 3.2-3.26 (m, 2H), 2.45-2.59 (m, 2H), 2.08-2.11 (m, 1H), 1.88-1.92 (m, 2H), 0.95-0.98 (m, 2H), 0.85-0.88 (m, 2H); LC: 100%; MS: m/z=510 (M+1).

Provenance & Evidence