Water → HCID 57964266, compound

HRID 2403540Notes

Reaction equation

HRID 2403540 reaction equation
S(O)(=O)(=O)C.O[CH2:7][CH2:8][CH:9]1[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:18]=1[N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:19][C:18]=1[N:27]1[CH2:32][CH2:31][N:30]([CH2:7][CH2:8][CH:9]2[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]2)[CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 63036152HCID 63036152, compoundHCID 86636043HCID 86636043, compound

Product 1

HCID 57964266HCID 57964266, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 11.6 g (52.66 mmol) of 4-(2-hydroxyethyl)cyclohexanone mesylate, of 13.72 g (55.27 mmol) of 1-(2-fluoro-5-trifluoromethylphenyl)piperazine and 8.37 g (60.65 mmol) of potassium carbonate in 220 mL of acetonitrile is refluxed overnight, then cooled back to room temperature. Water (80 mL) is added. Organics are extracted with ethyl acetate (100 mL). The organic phase is washed with water (20 mL), dried over magnesium sulfate and concentrated under reduced pressure to give a crude product. Purification by column chromatography over 320 g of silica gel (eluant dichloromethane/methanol 98/2 to 96/4) yields 15.86 g of 4-(2-fluoro-5-trifluoromethylphenyl)-1-[2-(4-oxocyclohexyl)ethyl]piperazine melting at 75-76° C.

Workup

  1. extractionOrganics are extracted with ethyl acetate (100 mL)
  2. washThe organic phase is washed with water (20 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a crude product
  6. customPurification by column chromatography over 320 g of silica gel (eluant dichloromethane/methanol 98/2 to 96/4)

Sources & evidence

ORD record
ord-ab43ddf3708b404687356d5011165d5e
Source dataset
uspto-grants-2014_08
Patent number
US08802678B2

Reaction notes

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