反应详情

温度

40 °C

N-(2-Methanesulfonyloxy-2-phenylethyl)-N-methylbenzenesulfonamide (128 mg, 0.346 mmol), spiro(benzo[b]thiophene-3(2H),4'-piperidine) (142 mg, 0.693 mmol), and sodium carbonate (167 mg, 1.04 mmol) were combined in 1.0 mL of dry DMF. The mixture was stirred under nitrogen 1 h at room temperature and 1.5 h at 40° C., then slowly warmed to 65° C. and maintained at that temperature for 5 h. After cooling to room temperature and stirring overnight, the mixture was partitioned between 50 mL of ethyl acetate and 25 mL of saturated aqueous sodium bicarbonate. The organic layer was washed with 25 mL of brine, dried over sodium sulfate and concentrated. Purification by preparative TLC, eluting with 5% ethyl ether in dichloromethane, gave 103 mg of the title compound as a viscous oil. 1NMR (400 MHz, CDCl3): δ 7.77 (d, 2H, J=8 Hz), 7.58 (tt, 1H, J=8, 1 Hz), 7.51 (t, 2H, J=8 Hz), 7.39-7.28 (m, 3H), 7.23 (d, 2H, J=8 Hz), 7.17-7.03 (m, 4H), 3.77 (t, 1H, J=7 Hz), 3.71 (dd, 1H, J=13, 7 Hz), 3.30 (dd, 1H, J=13, 7 Hz), 3.12 (d, 1H, J=11 Hz), 3.08 (d, 1H, J=11 Hz), 2.94 (bd, 1H, J=12 Hz), 2.84 (bd, 1H, J=12 Hz), 2.65 (s, 3H), 2.34 (td, 1H, J=12, 3 Hz), 1.99 (td, 1H, J=12, 3 Hz), 1.96-1.73 (m, 4H). Mass spectrum (ESE): m/z=479 (M+1).

1. temperatureslowly warmed to 65° C.
2. temperaturemaintained at that temperature for 5 h
3. temperatureAfter cooling to room temperature
4. stirringstirring overnight
5. customthe mixture was partitioned between 50 mL of ethyl acetate and 25 mL of saturated aqueous sodium bicarbonate
6. washThe organic layer was washed with 25 mL of brine
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated
9. customPurification by preparative TLC
10. washeluting with 5% ethyl ether in dichloromethane