Potassium Carbonate → tert-Butyl 4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carboxylate
Reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([OH:18])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])=[CH:5][CH:4]=1.[N:19]1([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:11][C:10]([F:13])([F:12])[C:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:22]2[CH2:21][CH2:20][N:19]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:24][CH2:23]2)=[CH:4][CH:5]=1)([OH:18])[C:14]([F:17])([F:16])[F:15]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
2-(4-(Bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (14.83 mmol, 5 g), tert-butyl piperazine-1-carboxylate (14.83 mmol, 2.76 g) and potassium carbonate (44.5 mmol, 6.15 g) were combined and stirred at room temperature overnight in acetonitrile (50 mL). The reaction mixture was filtered and the solvent removed at reduced pressure. The residue was taken up in ethyl acetate and washed with saturated sodium bicarbonate solution. The organic layer was dried over magnesium sulphate and concentrated under vacuum to afford the title compound (7.12 g).
Workup
- filtrationThe reaction mixture was filtered
- customthe solvent removed at reduced pressure
- washwashed with saturated sodium bicarbonate solution
- dry with materialThe organic layer was dried over magnesium sulphate
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-b7a222c171294c94b34eb559e1652548
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08357679B2
Reaction notes
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