Formaldehyde → HCID 68983737, compound

Participants

Reaction Steps

A mixture of (2S) N-cyclopropyl-N-[1-(4-methyl-2-methylamino-pentanoyl)piperidin-4-yl]-3-trifluoromethylbenzenesulfonamide (see Example 10, 323 mg, 0.7 mmol), methanol (4 mL), paraformaldehyde (50 mg, 1.0 mmol), NaBH3(CN) (132 mg, 2 mmol), and acetic acid (0.01 mL) was shaken at room temperature for 20 hours. The solvents were removed under vacuum. The residue was dissolved in dichloromethane (15 mL), and treated with aqueous saturated K2CO3 (5 mL). The organic layer was separated, washed with brine, concentrated under vacuum, and purified by column (silica gel, EtOAc/hexane 3/7) to give the title compound (2S) N-cyclopropyl-N-[1-(2-dimethylamino-4-methylpentanoyl)piperidin-4-yl]-3-trifluoromethyl-benzenesulfonamide as white solid (30 mg, yield 10%). 1H NMR (CDCl3): δ 8.14 (s, 1H), 8.08 (d, 1H, J=7.9 Hz), 7.87 (d, 1H, J=7.7 Hz), 7.7 (dd, 1H, J=7.7 & 8.1 Hz), 4.7-4.76 (m, 1H), 4.18-4.24 (m, 1H), 4.06-4.12 (m, 1H), 3.34-3.4 (m, 1H), 2.94-3.06 (m, 1H), 2.44-2.54 (m, 1H), 2.26 (br, 6H), 1.35-1.98 (m, 8H), 0.94-1.02 (m, 2H), 0.86-0.95 (m, 6H), 0.74-0.78 (m, 2H). LC: 100%. MS (e/z), 490 (m+1).

Provenance & Evidence