1,4-Cyclohexadiene → 4-(4-benzyl-5-methyl-1H-pyrazole-3(2H)-on-2-yl)-piperidine

HRID 1068181Notes

Reaction equation

HRID 1068181 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18](=[O:19])[C:17]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:16]([CH3:27])[NH:15]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C1CC=CCC=1>CCO.[OH-].[OH-].[Pd+2]>[CH2:20]([C:17]1[C:18](=[O:19])[N:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[NH:15][C:16]=1[CH3:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 211929481-benzyl-4-(4-benzyl-5-methyl-1H-pyrazol-3(2H)-on-2-yl)-piperidine

Product 1

HCID 211931254-(4-benzyl-5-methyl-1H-pyrazole-3(2H)-on-2-yl)-piperidineYield 110.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 0.52 g of 1-benzyl-4-(4-benzyl-5-methyl-1H-pyrazol-3(2H)-on-2-yl)-piperidine in 20 mL of EtOH under nitrogen was added 0.2 g of Pearlman's catalyst and 2.5 mL of 1,4-cyclohexadiene. This mixture was refluxed for 3 hours, filtered through Celite and concentrated under reduced pressure to give 0.43 g of 4-(4-benzyl-5-methyl-1H-pyrazole-3(2H)-on-2-yl)-piperidine. ESI-MS 271.9 (M+H); HPLC A: 1.68 min.

Workup

  1. temperatureThis mixture was refluxed for 3 hours
  2. filtrationfiltered through Celite
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f8923e7edbec4a84a198d058bd7969c0
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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