Trifluoroacetic acid → Piperidine, 4-[2-(trifluoromethoxy)phenyl]-

HRID 505125Notes

Reaction equation

HRID 505125 reaction equation
C([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][C:21]([F:24])([F:23])[F:22])[CH2:10][CH2:9]1)C1C=CC=CC=1.C(O)(C(F)(F)F)=O>CCO.[Pd]>[F:24][C:21]([F:22])([F:23])[O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 667439831-Benzyl-4-(2-trifluoromethoxy-phenyl)-1,2,3,6-tetrahydro-pyridine

Product 1

HCID 58808055Piperidine, 4-[2-(trifluoromethoxy)phenyl]-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-benzyl-4-(2-trifluoromethoxy-phenyl)-1,2,3,6-tetrahydro-pyridine (described herein below) in EtOH was added (0.2 wt %) 10% Pd/C, followed by (5 eq.) TFA in a sealed tube. The reaction mixture was stirred at 50° C. under 3.0 bar of H2 for 12 h. The reaction mixture was filtered over Celite and the filtrate evaporated down to dryness. Redissolution in EtOAc, washing with 1N NaHCO3 and concentration gave the crude product which was directly used for the next step.

Workup

  1. filtrationThe reaction mixture was filtered over Celite
  2. customthe filtrate evaporated down to dryness
  3. washRedissolution in EtOAc, washing with 1N NaHCO3 and concentration

Sources & evidence

ORD record
ord-5033171b8a434624a81d20981058fa8b
Source dataset
uspto-grants-2010_08
Patent number
US07781436B2

Reaction notes

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