Thiomorpholine → HCID 68986305, compound

Participants

Reaction Steps

N-Cyclopropyl-N-[1-(3-thiomorpholin-4-yl-hexanoyl)piperidin-4-yl]-3-trifluoromethylbenzenesulfonamide (41) was prepared as follows. N-cyclopropyl-N-(1-hex-2-enoyl-piperidin-4-yl)-3-trifluoromethyl-benzenesulfonamide (30) (250 mg, 0.56 mmol) and thiomorpholine (2 mL) were heated together at 130° C. for 3 days in a sealed Reacti-vial. The vial was cooled in ice and then the cooled mixture was evaporated to dryness in vacuo in a Speed-Vac®. The residue was chromatographed over flash silica eluting with ethyl acetate:hexane (1:1) to give the title compound 41 (110 mg, 36%) as a white solid. LC: 100%. MS: m/z=548.3, 549.3 (M+H). 1H NMR (400 MHz, CDCl3): (1:1 mixture of rotamers) δ 8.15 (1H, s), 8.06 (1H, d, J=7.5 Hz), 7.88 (1H, d, J=7.5 Hz), 7.70 (1H, t, J=7.5 Hz), 4.73 (1H, d, J=17.7 Hz), 4.10 (1H, m), 3.95 (1H, d, J=17.7 Hz), 3.05 (2H, m), 2.84 (2H, m), 2.74 (2H, m), 2.67-2.43 (6H, m), 2.15 (1H, m), 1.96 (1H, m), 1.75 (3H, m), 1.52-1.22 (4H, m), 0.98 (1H, m), 0.93-0.70 (6H, m).

Provenance & Evidence