Water → HCID 57448049, compound

HRID 2358119Notes

Reaction equation

HRID 2358119 reaction equation
F[C:2]1[C:7]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH3:21])[CH2:15][CH2:14]1.C[O-].[Na+].O.[C:26](OCC)(=[O:28])C>CN(C)C=O.CO>[CH3:26][O:28][C:2]1[C:7]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH3:21])[CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 11702233HCID 11702233, compound

Product 1

HCID 57448049HCID 57448049, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 4-[2-fluoro-3-(trifluoromethoxy)phenyl]-1-propylpiperidine (1.92 g, 6.3 mmol) in N,N-dimethylformamide (20 ml) was added a solution of sodium methoxide in methanol (30%, 3 ml) and the mixture was heated to 150° C. for 1 h. Water (50 ml) and ethyl acetate (50 ml) was added and the phases were separated. The aqueous phase was extracted with ethyl acetate (2×50 ml) and the combined organic phases was dried (MgSO4) and evaporated under reduced pressure to give an oil. The residue was purified by flash column chromatography (ethyl acetate/methanol, 1:1) to give the title compound (1.32 g). MS m/z (rel. intensity, 70 eV) 317 (M+, 6), 289 (17), 288 (bp), 204 (6), 175 (8).

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with ethyl acetate (2×50 ml)
  3. dry with materialthe combined organic phases was dried (MgSO4)
  4. customevaporated under reduced pressure
  5. customto give an oil
  6. customThe residue was purified by flash column chromatography (ethyl acetate/methanol, 1:1)

Sources & evidence

ORD record
ord-cd5beaf33b39482194d7d7d6a7811f51
Source dataset
uspto-grants-2010_07
Patent number
US07763639B2

Reaction notes

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