Water → Methyl 4-piperidin-1-yl-2-(trifluoromethyl)benzoate

HRID 217433Notes

Reaction equation

HRID 217433 reaction equation
F[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.O>CN(C=O)C>[N:22]1([C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 15541084Methyl 4-fluoro-2-(trifluoromethyl)benzoate

Product 1

HCID 58439025Methyl 4-piperidin-1-yl-2-(trifluoromethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 4-fluoro-2-(trifluoromethyl)benzoate in DMF were added K2CO3 and piperidine, followed by stirring at 100° C. for 3 hours. The reaction mixture was cooled to 0° C., and water was added thereto, followed by extraction with EtOAc. The organic layer was washed with brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:EtOAc=100:0 to 90:10) to obtain methyl 4-piperidin-1-yl-2-(trifluoromethyl)benzoate as a colorless oily substance.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. extractionfollowed by extraction with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:EtOAc=100:0 to 90:10)

Sources & evidence

ORD record
ord-caf402de862249dbac773b2155761377
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Reaction notes

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