Triethylamine → HCID 57959915, compound

Participants

Reaction Steps

To a solution of {1-[4-(propylsulphonyl)phenyl]-2-pyrrolidin-1-ylethyl}amine (100 mg, 0.337 mmol) in dichloromethane (5 mL) under nitrogen was added triethylamine (47 □L, 0.337 mmol) followed by 2,4-dichlorobenzoyl chloride (47 □L, 0.336 mmol). The mixture was stirred at ambient temperature for 2 h, then diluted with water and extracted with ethyl acetate (×2). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated. The product was purified by chromatography on silica eluting with 3% MeOH in dichloromethane to give the product as an off-white solid (123 mg, 78%). 1H NMR δ (400 MHz, CDCl3) δ 1.00 (3H, t, J=7.4 Hz), 1.69-1.81 (6H, m), 2.46-2.49 (2H, m), 2.58-2.62 (2H, m), 2.73 (1H, dd, J=12.5, 5.1 Hz), 2.91 (1H, dd, J=12.52, 9.5 Hz), 3.03-3.07 (2H, m), 5.01-5.09 (1H, m), 7.33 (1H, dd, J=8.3, 1.9 Hz), 7.46 (1H, d, J=1.9 Hz), 7.56 (2H, d, J=8.3 Hz), 7.64 (1H, d, J=8.3 Hz), 7.72 (1H, br d, J=3.9 Hz), 7.87 (2H, d, J=8.32 Hz); m/z (ES+) 471 (M+H), 469 (M+H), 400 (M-pyrrolidine), 398 (M-pyrrolidine).

Provenance & Evidence