1-Benzyl-4-[4-(trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine → 4-(4-(Trifluoromethyl)phenyl)piperidine

HRID 856053Notes

Reaction equation

HRID 856053 reaction equation
C([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)(=O)C.[Pd]>[F:23][C:20]([F:21])([F:22])[C:17]1[CH:16]=[CH:15][C:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 161275071-Benzyl-4-[4-(trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 124407024-(4-(Trifluoromethyl)phenyl)piperidineYield 105.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 1-benzyl-4-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine (528 mg, 1.66 mmol) prepared in Reference Example 96 and 10% palladium/carbon (50 mg) in acetic acid (5 ml) was stirred at room temperature under an atmospheric pressure of hydrogen. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure. The residue was dissolved in methylene chloride, and the mixture was washed with water, 10% sodium hydroxide aqueous solution and brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to afford 4-(4-trifluoromethylphenyl)piperidine (400 mg, quantitative) as a yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washthe mixture was washed with water, 10% sodium hydroxide aqueous solution and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-589d798b66ac4c7b8502b5cad0513ffd
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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