Ethyl Acetate → 4-[4-(2-Oxazolin-2-yl)benzyl]-1-(4-trifluoromethylbenzoyl)piperidine

HRID 129092Notes

Reaction equation

HRID 129092 reaction equation
[O:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:30]=[CH:29][C:9]([CH:10]=[C:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:28])[C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)[CH2:13][CH2:12]2)=[CH:8][CH:7]=1.[H][H].C(OCC)(=O)C>C(O)C.[C].[Pd]>[O:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:30]=[CH:29][C:9]([CH2:10][CH:11]2[CH2:12][CH2:13][N:14]([C:17](=[O:28])[C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:25])([F:26])[F:27])=[CH:20][CH:19]=3)[CH2:15][CH2:16]2)=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 152313864-[4-(2-Oxazolin-2-yl)benzylidene]-1-(4-trifluoromethylbenzoyl)piperidineHCID 178418361HCID 178418361, compound

Product 1

HCID 152313944-[4-(2-Oxazolin-2-yl)benzyl]-1-(4-trifluoromethylbenzoyl)piperidine

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

441 mg (1 mmol) of 4-[4-(2-oxazolin-2-yl)benzylidene]-1-(4-trifluoromethylbenzoyl)piperidine are hydrogenated (ambient temperature, 30 minutes, hydrogen pressure 50 psi) in 10 ml of anhydrous ethanol and 2.5 ml of ethyl acetate in the presence of 0.5 g of palladium-carbon (10%). The catalyst is then suction-filtered, the filtrate is evaporated under reduced pressure at a bath temperature of 50° C. and the residue is purified by column chromatography (Silica gel; ethyl acetate). 200 mg (48% of theory) of the title compound of melting point 115° C. are obtained.

Workup

  1. filtrationThe catalyst is then suction-filtered
  2. customthe filtrate is evaporated under reduced pressure at a bath temperature of 50° C.
  3. customthe residue is purified by column chromatography (Silica gel; ethyl acetate)

Sources & evidence

ORD record
ord-86e54884df594b6f9f2f01f4ed97cdcc
Source dataset
uspto-grants-1995_11
Patent number
US05466687

Reaction notes

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