Water → N-[1-(2-phenylethyl)-4-piperidyl]-4-(N-acetyl-N-methylamino)benzenesulfonamide
Reaction equation
C(O)(=O)C.[NH:5]1[CH2:10][CH2:9][CH:8]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([N:21]([C:23](=[O:25])[CH3:24])[CH3:22])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:7][CH2:6]1.[I-].[K+].Br[CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.O>C(=O)([O-])O.[Na+].CN(C)C=O>[C:31]1([CH2:30][CH2:29][N:5]2[CH2:6][CH2:7][CH:8]([NH:11][S:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]([C:23](=[O:25])[CH3:24])[CH3:22])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH2:9][CH2:10]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
The N-(4-piperidyl)-4-(N-acetyl-N methylamino)benzenesulfonamide acetate (3.71 g, 10.6 mmol) prepared in Preparative Example 17 was dissolved in a suspension of sodium hydrogencarbonate (2.52 g) and potassium iodide (3.32 g) in dimethylformamide (50 ml), followed by the addition of 2-bromoethylbenzene (1.49 ml, 11.0 mmol). The obtained mixture was stirred at 70° C. for 3 hours, followed by the addition of water. The obtained mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of common salt, dried over magnesium sulfate, and concentrated to give N-[1-(2-phenylethyl)-4-piperidyl]-4-(N-acetyl-N-methylamino)benzenesulfonamide as a colorless oil (3.19 g, yield: 77%).
Workup
- extractionThe obtained mixture was extracted with ethyl acetate
- washThe organic layer was washed with water
- dry with materiala saturated aqueous solution of common salt, dried over magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6f939988d198467d97e392abed14aa74
- Source dataset
- uspto-grants-1994_01
- Patent number
- US05281626
Reaction notes
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