Diisopropylethylamine → 4-(4-Trifluoromethoxy-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester
Reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[F:23][C:24]([F:37])([F:36])[O:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>C(Cl)Cl>[F:37][C:24]([F:23])([F:36])[O:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)(=[O:34])=[O:33])=[CH:28][CH:27]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1,1-dimethylethyl 1-piperazinecarboxylate (5 g, 19.19 mmol, supplier Aldrich), in DCM (80 mL), DIPEA (5.03 mL, 28.8 mmol) was added under argon atmosphere at room temperature then 4-[(trifluoromethyl)oxy]benzenesulfonyl chloride (2.326 mL, 19.19 mmol) was added at 0° C. then ice bath was removed and the reaction mixture was stirred for 3 hrs. The reaction mixture was partitioned between DCM (30 ml) and sodium bicarbonate (2×20 ml). The organic phase was washed with HCl (2×20 ml) and water (2×20 ml), then it was dried using phase separator and DCM was removed under vacuum to give the title compound (5.5 g) as a yellow viscous liquid.
Workup
- customice bath was removed
- customThe reaction mixture was partitioned between DCM (30 ml) and sodium bicarbonate (2×20 ml)
- washThe organic phase was washed with HCl (2×20 ml) and water (2×20 ml)
- customit was dried
- customwas removed under vacuum
Sources & evidence
- ORD record
- ord-b0511dfbe22e4628bb1cfc0566ef05b5
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08697703B2
Reaction notes
Loading…