N-(1-benzylpiperidin-4-yl)-2,2,2-trifluoroacetamide → 2,2,2-trifluoro-N-(piperidin-4-yl)acetamide

HRID 1634060Notes

Reaction equation

HRID 1634060 reaction equation
C([O-])=O.[NH4+].[F:5][C:6]([F:24])([F:23])[C:7]([NH:9][CH:10]1[CH2:15][CH2:14][N:13](CC2C=CC=CC=2)[CH2:12][CH2:11]1)=[O:8]>[Pd].CO>[F:24][C:6]([F:5])([F:23])[C:7]([NH:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)=[O:8]

Participants

5

Reactant 2

HCID 1531300N-(1-benzylpiperidin-4-yl)-2,2,2-trifluoroacetamideHCID 2723923Ammonium formate

Product 1

HCID 107742532,2,2-trifluoro-N-(piperidin-4-yl)acetamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Conditions

Temperature
5 °C

Procedure

A 500 mL, three-necked round-bottomed flask under nitrogen was charged with 4 g of 10% Palladium on Carbon, and 100 mL of methanol. The suspension was cooled to 5° C. and 10 g of ammonium formate was added in one batch (evolution of gas was observed). A solution of 10 g (35 mmol) of the 4-trifluoroacetamido-1-benzylpiperidine in 100 mL of methanol was then added dropwise gradually. The resulting reaction mixture was refluxed for 2.5 hr. and then at room temperature overnight. The catalyst was filtered off through Celite under a blanket of nitrogen and washed with ethanol. The filtrate was concentrated under reduced pressure to give 6.9 g (quantitative yield) of a light yellow solid of the title compound.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 2.5 hr
  3. customat room temperature
  4. customovernight
  5. filtrationThe catalyst was filtered off through Celite under a blanket of nitrogen
  6. washwashed with ethanol
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-dfd2ecebe6804fa5b1cb67b841bed5d8
Source dataset
uspto-grants-2003_01
Patent number
US06506749B2

Reaction notes

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