4-Toluenesulfonyl chloride → 1-[(4-Methylphenyl)sulfonyl]-4-phenylpiperidine
Reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(#N)C>[CH3:30][C:20]1[CH:25]=[CH:24][C:23]([S:26]([N:10]2[CH2:9][CH2:8][CH:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:12][CH2:11]2)(=[O:28])=[O:27])=[CH:22][CH:21]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of 4-phenylpiperidine (5.0 g) in acetonitrile (100 ml) was added triethylamine (8.64 ml) and then was added dropwise at 0° C. a solution of p-toluenesulfonyl chloride (6.50 g) in acetonitrile (30 ml). The mixture was stirred at 0° C. for 2 hours. Under reduced pressure, the solvent was evaporated, and to the residue was water. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the mixture was concentrated, and the resulting crystals were collected by filtration, which were washed with hexane to give colorless crystals of 1-(4-methylphenylsulfonyl)-4-phenylpiperidine (8.93 g).
Workup
- customUnder reduced pressure, the solvent was evaporated
- extractionThe mixture was extracted with ethyl acetate
- washthe organic layer was washed with saturated brine
- dry with materialdried with magnesium sulfate
- concentrationUnder reduced pressure, the mixture was concentrated
- filtrationthe resulting crystals were collected by filtration, which
- washwere washed with hexane
Sources & evidence
- ORD record
- ord-0ac11c67b5db44359fa3aad6cd4e8e2a
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06172061B2
Reaction notes
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