Dimethylamine → HCID 68984178, compound

Participants

Reaction Steps

N-cyclopropyl-N-(1-hex-2-enoyl-piperidin-4-yl)-3-trifluoromethyl-benzenesulfonamide (30) (250 mg, 0.56 mmol) and dimethylamine in methanol (2M, 3 mL) were heated in a sealed React-vial at 120° C. for 24 hours. The cooled solution was evaporated to dryness in vacuo and the residue chromatographed over flash silica eluting with ethyl acetate (3× column lengths) followed by ethyl acetate:methanol:ammonia (100:10:1) to give the title compound 44 (150 mg, 34%) as a white solid. TLC (SiO2, ethyl acetate: methanol: ammonia, 100:10:1) Rf=0.15 (UV detection, Dragendorff's reagent). LC: 100%. MS: m/z=490.3, 491.2 (M+H). 1H NMR (400 MHz, CDCl3): (1:1 mixture of rotamers) δ 8.14 (1H, s), 8.07 (1H, d, J=8 Hz), 7.88 (1H, d, J=8 Hz), 7.70 (1H, t, J=8 Hz), 4.74 (1H, d, J=12 Hz), 4.07 (1H, m), 3.95 (1H, d, J=12 Hz), 3.05 (2H, m), 2.50 (2H, m), 2.24 (6H, s), 2.15 (1H, 2d), 1.96 (1H, m), 1.86-1.69 (3H, m), 1.58-1.24 (6H, m), 0.98 (1H, m), 0.90 (3H, t, J=8 Hz), 0.87-0.75 (3H, m).

Provenance & Evidence