tert-Butyl piperazine-1-carboxylate → 4-(3-Fluoro-4-trifluoromethyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester
Reaction equation
CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29].Cl[C:42]1[CH:47]=[CH:46][C:45]([C:48]([F:51])([F:50])[F:49])=[C:44]([F:52])[CH:43]=1>CCOCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][N:38]([C:42]2[CH:47]=[CH:46][C:45]([C:48]([F:50])([F:51])[F:49])=[C:44]([F:52])[CH:43]=2)[CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:29])[CH3:30]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
To a mixture of sodium tert-butoxide (0.68 g, 6.9 mmol), palladium(II) acetate (11 mg, 0.05 mmol), 2-(di-t-butylphosphino)biphenyl (149 mg, 0.49 mmol), tert-Butyl-1-piperazine carboxylate (1.1 g, 5.9 mmol) and 4-chloro-2-fluorobenzotrifluoride (1 g, 4.94 mmol) was added degazed toluene (10 ml). The mixture was heated to 80° C. overnight. The mixture was cool to room temperature, diluted with ether, filtered and the filtrate was concentrated in vacuo. The residue was chromatographed over silica gel: eluent: Heptane/Ethylacetate 0-10% over 15 minutes to provide the title compound (1.05 g, 61%) as a white solid, MS (m/e): 349.2 (M+H, 100%).
Workup
- temperatureThe mixture was cool to room temperature
- filtrationfiltered
- concentrationthe filtrate was concentrated in vacuo
- customThe residue was chromatographed over silica gel
Sources & evidence
- ORD record
- ord-7b3e9962b4ad40f397d513f67e08fa95
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07595314B2
Reaction notes
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