3-(4-Fluorobenzoyl)propyl chloride → HCID 57664586, compound

Participants

Reaction Conditions

Reaction Steps

N-Cyclopropyl-N-{1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl}benzenesulfonamide (39) was prepared as follows. A mixture of N-cyclopropyl-N-(4-piperidinyl)benzenesulfonamide (100 mg, 0.36 mmol), 4-chloro-4′-fluorobutyrophenone (79 mg, 0.39 mmol) and TEA (54 mg, 0.54 mmol) in DMF was heated at 70° C. for 36 hours. The solvent was removed and the crude product was purified on a silica gel column, eluting first with CH2Cl2, then with EtOAc and 10% MeOH/EtOAc, to afford the title compound 39 as an orange oil. 1H NMR (CDCl3): δ 8.006-7.956 (m, 2H), 7.868-7.844 (d, 2H), 7.599-7.556 (m, 1H), 7.535-7.490 (m, 2H), 7.147-7.089 (t, 2H), 3.855-3.773 (m, 1H), 2.950-2.871 (m, 4H), 2.421-2.330 (t, 2H), 2.020-1.772 (m, 7H), 1.518-1.454 (d, 2H), 0.950-0.910 (m, 2H), 0.730-0.682 (m, 2H). LC: 98%. MS (e/z): 446 (M+H+).

Provenance & Evidence