Water → Tert-butyl 4-(4-phenyl-1,3-thiazol-2-yl)piperazine-1-carboxylate
Reaction equation
Cl[C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:7]1([C:5]2[N:6]=[C:2]([N:23]3[CH2:22][CH2:21][N:20]([C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])[CH2:25][CH2:24]3)[S:3][CH:4]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1Participants
6
Procedure
A solution of 2-chloro-4-phenyl-1,3-thiazole (1.54 mg, 7.87 mmol), 1-(tert-butoxycarbonyl)-piperazine (4.40 g, 23.6 mmol) and potassium carbonate (1.09 g, 7.87 mmol) in dimethylformamide (26 ml) was stirred at 120° C. for 2 hours. Water was poured to the reaction mixture, and the resulting solution 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=9:1) to give 691 mg (25.4%) of tert-butyl 4-(4-phenyl-1,3-thiazol-2-yl)piperazine-1-carboxylate as a solid.
Workup
- extractionthe resulting solution 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=9:1)
Sources & evidence
- ORD record
- ord-951dbc3ab50141feb4c806e0575a73a6
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07851473B2
Reaction notes
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