Dimethylformamide → Tert-butyl 4-(4-phenyl-1,3-thiazol-2-yl)piperidine-1-carboxylate
Reaction equation
[NH2:1][C:2]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)=[S:3].Br[CH2:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=O.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:21]1([C:19]2[N:1]=[C:2]([CH:4]3[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]3)[S:3][CH:18]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
A mixture of tert-butyl 4-(aminocarbonothioyl)piperidine-1-carboxylate (1.00 g, 7.24 mmol), 2-bromoacetophenone (1.58 g, 7.96 mmol), potassium carbonate (1.00 g, 7.24 mmol) and N,N-dimethylformamide (30 ml) was stirred at 110° C. for 1.5 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 purified by silica gel column chromatography (hexane: ethyl acetate=1:1) to obtain the desired product (1.38 g, 55.2%) as an oil.
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 purified by silica gel column chromatography (hexane: ethyl acetate=1:1)
Sources & evidence
- ORD record
- ord-456f5b70f02a4089afc513f701048882
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07851473B2
Reaction notes
Loading…