Triethylamine → HCID 22220427, compound

Participants

Reaction Steps

To a stirred solution of 1-(4-amino-phenyl)-piperidin-4-one hydrochloride (which was obtained in Example 224) (8.76 g, 0.32 mol) in methylene chloride (100 mL) at room temperature was added triethylamine (9 mL). To this mixture was added a mixture of 3-pyridinesulfonyl chloride (7.45 g, 0.035 mol) and triethylamine (9 mL). The reaction was stirred for 18 hours. The reaction mixture was concentrated. The product was flash silica gel chromatographed eluting with 7:3 ethyl acetate/hexanes and then flash silica gel chromatographed eluting with 3% methanol in methylene chloride to give the titled compound as a yellow solid (1.34 g, 13%); 1H NMR (300 MHz, CDCl3) δ 2.54(t, J=6 Hz, 4 H), 3.56(t, J=6 Hz, 4 H), 6.79(s, 1 H), 6.85(d, J=12 Hz, 2 H), 6.98(d, J=12 Hz, 2 H), 7.40(m, 1H), 7.97(dd, J=3 Hz, 1 H), 8.75(dd, J=6 Hz, 1 H), 8.90(d, J=3 Hz, 1 H); MS (ES) m/z: 331.9 (MH+, 100%); HRMS Calcd. for C16H17N3O3S (MH+): 332.1063. Found: 332.1063.

Provenance & Evidence