Sodium Carbonate → N-Methyl-N-(2-phenyl-2-(spiro(benzo[b]thiophene-3(2H),4'-piperidin)-1'-yl)ethyl)benzenesulfonamide

HRID 1737452Notes

Reaction equation

HRID 1737452 reaction equation
CS(O[CH:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:7][N:8]([CH3:18])[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:11])=[O:10])(=O)=O.[NH:25]1[CH2:30][CH2:29][C:28]2([CH2:34][S:33][C:32]3[CH:35]=[CH:36][CH:37]=[CH:38][C:31]2=3)[CH2:27][CH2:26]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[CH3:18][N:8]([CH2:7][CH:6]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[N:25]1[CH2:30][CH2:29][C:28]2([CH2:34][S:33][C:32]3[CH:35]=[CH:36][CH:37]=[CH:38][C:31]2=3)[CH2:27][CH2:26]1)[S:9]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)(=[O:10])=[O:11]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 18388382spiro(benzo[b]thiophene-3(2H),4'-piperidine)HCID 21842580HCID 21842580, compound

Product 1

HCID 21842587N-Methyl-N-(2-phenyl-2-(spiro(benzo[b]thiophene-3(2H),4'-piperidin)-1'-yl)ethyl)benzenesulfonamideYield 62.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-9cbe7b2f32fe49e0be0b09f1f2c3e31e
Source dataset
uspto-grants-1999_10
Patent number
US05962462

Reaction notes

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