Dimethylformamide → Tert-butyl 4-(1-{[3-(trifluoromethyl)phenyl]thio}ethyl)piperidine-1-carboxylate
Reaction equation
CS(O[CH:6]([CH:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1)[CH3:7])(=O)=O.[F:21][C:22]([F:31])([F:30])[C:23]1[CH:24]=[C:25]([SH:29])[CH:26]=[CH:27][CH:28]=1.C([O-])([O-])=O.[K+].[K+].CN(C)C=O>CCOCC>[F:31][C:22]([F:21])([F:30])[C:23]1[CH:24]=[C:25]([S:29][CH:6]([CH:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:12][CH2:13]2)[CH3:7])[CH:26]=[CH:27][CH:28]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a 250 ml round bottom flask was added tert-butyl 4-{1-[(methylsulfonyl)oxy]ethyl}piperidine-1-carboxylate (11 g, 35.8 mmol), 3-(trifluoromethyl)benzenethiol (7.6 g, 43 mmol), K2CO3 (9.9 g, 72 mmol) and 80 ml dimethylformamide. The reaction mixture was heated at 50° C. for 36 hr under N2, then cooled down to room temperature, 150 ml ether was added. The resulting mixture was sequentially washed with 250 ml water, 100 ml 5% KOH solution and 75 ml brine. The organic layers were dried over sodium sulfate, filtered and concentrated to give 13.7 g crude product. It was used for next step without further purification.
Workup
- temperaturecooled down to room temperature
- washThe resulting mixture was sequentially washed with 250 ml water, 100 ml 5% KOH solution and 75 ml brine
- dry with materialThe organic layers were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-bae8fcf665914e04aa030ac3dde3af67
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08304434B2
Reaction notes
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