Acetic Acid → 5-[4-(Trifluoromethyl)phenyl]piperidine-3-carboxamide acetate

HRID 1642810Notes

Reaction equation

HRID 1642810 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([C:15]([NH2:17])=[O:16])[CH:12]=[N:13][CH:14]=2)=[CH:5][CH:4]=1.[H][H].[C:22]([OH:25])(=[O:24])[CH3:23]>[Pd]>[C:22]([OH:25])(=[O:24])[CH3:23].[F:18][C:2]([F:1])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][NH:13][CH2:12][CH:11]([C:15]([NH2:17])=[O:16])[CH2:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 99000085-(4-(Trifluoromethyl)phenyl)nicotinamideHCID 178418361HCID 178418361, compound

Product 1

HCID 667551875-[4-(Trifluoromethyl)phenyl]piperidine-3-carboxamide acetate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Palladium on activated carbon (moistened with about 50% water, 0.3 g/mmol) was added to a solution of 500 mg (1.88 mmol) of 5-[4-(trifluoromethyl)phenyl]pyridine-3-carboxamide (Example 50A) in 60 ml of acetic acid, and the mixture was hydrogenated in a 60 bar hydrogen atmosphere at 85° C. overnight. The catalyst was then filtered off through a filter layer and washed repeatedly with ethanol. The combined filtrates were concentrated under reduced pressure. This gave 0.61 g (98% of theory) of the target compound, which was reacted without any further purification steps.

Workup

  1. filtrationThe catalyst was then filtered off through a filter layer
  2. washwashed repeatedly with ethanol
  3. concentrationThe combined filtrates were concentrated under reduced pressure
  4. customThis gave 0.61 g (98% of theory) of the target compound, which was reacted without any further purification steps

Sources & evidence

ORD record
ord-80f177d646144cbbbdf4dcbd5de47ea7
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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