Cyclohexene → 5-Methyl-N-(piperidin-4-yl)-nicotinamide

HRID 502357Notes

Reaction equation

HRID 502357 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:23])[C:16]2[CH:21]=[C:20]([CH3:22])[CH:19]=[N:18][CH:17]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C1CCCCC=1>CCO.[OH-].[OH-].[Pd+2]>[CH3:22][C:20]1[CH:19]=[N:18][CH:17]=[C:16]([CH:21]=1)[C:15]([NH:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)=[O:23]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 68456038HCID 68456038, compound

Product 1

HCID 655621085-Methyl-N-(piperidin-4-yl)-nicotinamideYield 102.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

N-(1-Benzyl-piperidin-4-yl)-5-methyl-nicotinamide (1.3 g, 4 mmol), Pd(OH)2/C (0.1 g) and cyclohexene (2 ml) were heated at reflux in EtOH (15 mL) for 2 h, after which time the reaction was filtered hot through a pad of Hyflo. The filtrate was concentrated to afford the title compound as a white powder (0.9 g, 98%).

Workup

  1. filtrationafter which time the reaction was filtered hot through a pad of Hyflo
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-656a297150b349e2bccb4f3c86914763
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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