Cesium carbonate → HCID 58425605, compound

HRID 1966433Notes

Reaction equation

HRID 1966433 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[C:12](=[O:15])([O-])[O-].[Cs+].[Cs+].[C:18]1([C:24]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN1C(=O)CCC1.O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:29]2[CH2:28][CH2:27][N:26]([C:24]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:25])[CH2:31][CH2:30]2)=[CH:3][C:4]=1[O:15][C:12]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 7626541-BenzoylpiperazineHCID 27833624-Bromo-2-fluoro-1-nitrobenzene

Product 1

HCID 58425605HCID 58425605, compoundYield 130.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 4-bromo-2-fluoro-1-nitrobenzene (0.6 g, 2.75 mmol) phenol (0.28 g, 3.02 mmol) and cesium carbonate (1.8 g, 5.5 mmol) in NMP (6 mL) was heated at 70° C. for 12 h, cooled then diluted with H2O (15 mL) and extracted with ethyl acetate (3×10 mL). The organics were washed with brine (8 mL), dried (Na2SO4) then filtered and concentrated in vacuo. The colorless solid was dissolved in NMP (2 mL) to which was added phenyl(piperazin-1-yl)methanone (1.0 g, 5.5 mmol) and the solution was heated to 110° C. for 16 h. The mixture was cooled and then diluted with H2O (15 mL) and extracted with ethyl acetate (3×10 mL). The organics were washed with brine (8 mL), dried (Na2SO4) then filtered and concentrated in vacuo. The residue was subjected to silica gel column chromatography (20% ethyl acetate/hexane) to furnish (4-(4-nitro-3-phenoxyphenyl)piperazin-1-yl)(phenyl)methanone (0.72 g, 1.8 mmol) as a yellow gum, 65% yield. 1H NMR (500 MHz, CDCl3) d (ppm) 8.11 (d, J=9.5 Hz, 1H), 7.51-7.47 (m, 5H), 7.39 (t, J=8.0 Hz, 2H), 7.18 (t, J=7.5 Hz, 1H), 7.05 (m, 2H), 6.64 (dd, J=2.5 Hz, 9.5 Hz, 1H), 6.35 (d, J=2.5 Hz, 1H), 4.1-3.1 (m, 8H).+ESI HRMS (calcd for C23H21N3NaO4, M+Na) 426.1430, found 426.1424

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate (3×10 mL)
  3. washThe organics were washed with brine (8 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationthen filtered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe colorless solid was dissolved in NMP (2 mL) to which
  8. temperatureThe mixture was cooled
  9. extractionextracted with ethyl acetate (3×10 mL)
  10. washThe organics were washed with brine (8 mL)
  11. dry with materialdried (Na2SO4)
  12. filtrationthen filtered
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-46449538ef924d0e9a79a8fe9f68a536
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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