Cyclohexene → N-(Piperidin-4-yl)-4'-(trifluoromethyl)-biphenyl-2-carboxamide

HRID 1167099

Reaction equation

HRID 1167099 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[C:18]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:16])[CH2:10][CH2:9]1)C1C=CC=CC=1.C1CCCCC=1>C(O)C.CO.[OH-].[Pd+2].[OH-]>[NH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[C:18]([C:23]3[CH:24]=[CH:25][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:27][CH:28]=3)=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:16])[CH2:10][CH2:9]1

Participants

6

Reactant 2

HCID 8079CyclohexeneHCID 229956921-Benzyl-4-(4'-trifluoromethylbiphenyl-2-carbonylamino)piperidine

Product 1

HCID 9928271N-(Piperidin-4-yl)-4'-(trifluoromethyl)-biphenyl-2-carboxamide

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

31.6 g (0.072 mol) of 4′-trifluoromethyl-biphenyl-2-carboxylic acid-(1-benzyl-piperidin-4-yl)-amide are dissolved in 180 ml ethanol and 180 ml methanol, mixed with 84 ml (0.83 mol) of cyclohexene and 6.53 g of palladium hydroxide (20% on charcoal) and refluxed for four hours. The hot reaction mixture is filtered through kieselguhr and the reaction mixture is concentrated by rotary evaporation.

Workup

  1. temperaturerefluxed for four hours
  2. filtrationThe hot reaction mixture is filtered through kieselguhr
  3. concentrationthe reaction mixture is concentrated by rotary evaporation

Sources & evidence

ORD record
ord-106d94eed4db4e3c9eaca0aec285400e
Source dataset
uspto-grants-2003_09
Patent number
US06617325B1

Linked notes

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