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

HRID 380480Notes

Reaction equation

HRID 380480 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH:14]=2)=[CH:5][CH:4]=1>CO.[Pd]>[F:16][C:2]([F:1])([F:15])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 12440708Pyridine, 1,2,3,6-tetrahydro-4-[4-(trifluoromethyl)phenyl]-

Product 1

HCID 124407024-(4-(Trifluoromethyl)phenyl)piperidineYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.54 g (1.22 mmol) of 4-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine and 0.1 g of 10% Pd/C in 20 mL of MeOH was stirred under a hydrogen atmosphere at 45 psi for 4 h. The reaction mixture was filtered through a thin pad of celite eluting with CH2Cl2. The solution was concentrated to give 0.26 g of the title compound.

Workup

  1. filtrationThe reaction mixture was filtered through a thin pad of celite
  2. washeluting with CH2Cl2
  3. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-e2659be6bccf4fb68b96db1a72af2b83
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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