Cesium carbonate → Tert-butyl 4-[4-(trifluoromethoxy)phenyl]piperazine-1-carboxylate

HRID 32705

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:53]([O:57][C:58]([N:60]1[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]1)=[O:59])([CH3:56])([CH3:55])[CH3:54].Br[C:67]1[CH:72]=[CH:71][C:70]([O:73][C:74]([F:77])([F:76])[F:75])=[CH:69][CH:68]=1>C(OC(=O)C)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[C:53]([O:57][C:58]([N:60]1[CH2:65][CH2:64][N:63]([C:67]2[CH:68]=[CH:69][C:70]([O:73][C:74]([F:75])([F:76])[F:77])=[CH:71][CH:72]=2)[CH2:62][CH2:61]1)=[O:59])([CH3:56])([CH3:54])[CH3:55]

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of cesium carbonate (1.88 g, 5.7 mmol), palladium(II)acetate (46.1 mg, 0.205 mmol), rac-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (192 mg, 0.31 mmol), tert-Butyl-1-piperazine carboxylate (928 mg, 4.93 mmol) and 1-Bromo-4-(trifluoromethoxy)benzene (1 g, 4.11 mmol) was added degazed toluene (10 ml). The mixture was heated to 100° C. for 4 hours. The mixture was cool to room temperature, diluted with ethylacetate, filtered and the solvent was removed in vacuo. The crude oil was chromatographed over silica gel: eluent: heptane/ethylacetate 0-10% over 20 minutes to provide the title compound (180 mg, 13%) as a yellow solid, MS (m/e): 347.4 (M+H, 100%).

Workup

temperatureThe mixture was cool to room temperature
filtrationfiltered
customthe solvent was removed in vacuo
customThe crude oil was chromatographed over silica gel

Sources & evidence

ORD record: ord-b45b3fee9e4a4e5f8550d6537c6cfb9b
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427612B2

Linked notes

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