Trifluoroacetic acid → 4-(4-(Trifluoromethyl)phenyl)piperidine

HRID 716885Notes

Reaction equation

HRID 716885 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(O)(C(F)(F)F)=O>CO.[C].[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

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 6139654-(4-Trifluoromethylphenyl)pyridine

Product 1

HCID 124407024-(4-(Trifluoromethyl)phenyl)piperidineYield 68.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A suspension of 4-(4-(trifluoromethyl)phenyl)pyridine (500 mg, 2.24 mmol, 1.00 equiv), CF3COOH (1.27 g, 11.14 mmol, 5.00 equiv), and palladium carbon (100 mg, 5%) in methanol (50 mL) was hydrogenated overnight under an atmosphere of H2(g) at 30° C. in an oil bath. The reaction mixture was filtered and washed with methanol and concentrated in vacuo. The pH value of the solution was adjusted to 8-9 with aqueous sodium hydroxide (1 M). The resulting solution was extracted with 3×20 mL of dichloromethane and the organic layers combined and concentrated under vacuum, yielding 350 mg (68%) of 4-(4-(trifluoromethyl)phenyl)piperidine as brown oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with methanol
  3. concentrationconcentrated in vacuo
  4. extractionThe resulting solution was extracted with 3×20 mL of dichloromethane
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0a839b13722b42b18b27e28509970855
Source dataset
uspto-grants-2015_11
Patent number
US09193693B2

Reaction notes

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