N-(1-benzylpiperidin-4-yl)-4-fluorobenzamide → 4-fluoro-N-(piperidin-4-yl)benzamide

HRID 49775

Reaction equation

HRID 49775 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:23])[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1>[Pd].CO>[NH:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15](=[O:23])[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 1

HCID 702501N-(1-benzylpiperidin-4-yl)-4-fluorobenzamide

Product 1

HCID 47782264-fluoro-N-(piperidin-4-yl)benzamideYield 97.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-(1-benzylpiperidin-4-yl)-4-fluorobenzamide (937 mg) and 10% palladium on carbon (50% wet, 0.2 g) in methanol (20 ml) was stirred under hydrogen atmosphere for 7.5 hours at ambient temperature. The catalyst was removed by glass filter and the solvent was removed under reduced pressure. After rinse with diisopropyl ether, N-(piperidin-4-yl)-4-fluorobenzamide (653 mg) was obtained.

Workup

  1. customThe catalyst was removed by glass
  2. filtrationfilter
  3. customthe solvent was removed under reduced pressure
  4. washAfter rinse with diisopropyl ether

Sources & evidence

ORD record
ord-86d50f487be049008b0004230cdd7116
Source dataset
uspto-grants-2004_03
Patent number
US06710043B1

Linked notes

Loading…