Cesium carbonate → HCID 67513524, compound

HRID 340630Notes

Reaction equation

HRID 340630 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.FC(F)(F)S(O[CH2:20][C:21]([F:24])([F:23])[F:22])(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:20][C:21]([F:24])([F:23])[F:22])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 27356291-(4-Bromophenyl)piperazine

Product 1

HCID 67513524HCID 67513524, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1-(4-bromophenyl)piperazine (1.24 g, 5.16 mmol) in DCM were added 2,2,2-trifluoroethyl trifluoromethanesulfonate (1.20 mL, 7.22 mmol) and cesium carbonate (5.04 g, 15.0 mmol). The resulting mixture was stirred for 30 min. The reaction mixture was then quenched with saturated aqueous ammonium chloride solution, extracted with ethyl acetate, the organic layer was collected and concentrated in vacuo. Purification by chromatography on silica gel (0 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 324.8 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 7.34 (d, J=9.1 Hz, 2 H),6.78 (d, J=9.0 Hz, 2 H),3.19-3.16 (m, 4 H),3.03 (q, J=9.5 Hz, 2 H),2.84-2.81 (m, 4 H).

Workup

  1. customThe reaction mixture was then quenched with saturated aqueous ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. customthe organic layer was collected
  4. concentrationconcentrated in vacuo
  5. customPurification by chromatography on silica gel (0 to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e8de94d6166f46619ca03f70a3baf8f3
Source dataset
uspto-grants-2014_11
Patent number
US08895583B2

Reaction notes

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