Dimethyl Sulfoxide → 4-(4-Phenyl-1,3-thiazol-2-yl)-N-pyridin-3-ylpiperidine-1-carboxamide
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[O:15])OCC(Cl)(Cl)Cl)[CH:2]=1.[C:16]1([C:22]2[N:23]=[C:24]([CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[S:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[C:16]1([C:22]2[N:23]=[C:24]([CH:27]3[CH2:32][CH2:31][N:30]([C:8]([NH:7][C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)=[O:15])[CH2:29][CH2:28]3)[S:25][CH:26]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2,2,2-trichloroethyl pyridin-3-ylcarbamate (187 mg, 0.696 mmol), 4-(4-phenyl-1,3-thiazol-2-yl)piperidine (170 mg, 0.696 mmol), diisopropylethylamine (0.121 ml, 0.696 mmol) and dimethylsulfoxide (3 ml) was stirred at 70° C. for 12 hours, the reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of hexane and ethyl acetate to obtain the desired product (84.0 mg, 33.1%) as a solid.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe residue was recrystallized from a mixed solvent of hexane and ethyl acetate
Sources & evidence
- ORD record
- ord-21afee884bdb43a8adc5ee62a9be0ade
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07851473B2
Reaction notes
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