1,4-Cyclohexadiene → HCID 54425483, compound

HRID 1017194Notes

Reaction equation

HRID 1017194 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]([C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][C:20]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:18])[CH2:12]1)=O)C1C=CC=CC=1.C1CC=CCC=1>C(O)C.[Pd]>[C:28]1([C:20]2[NH:21][C:22]3[C:27]([C:19]=2[C:17]([CH:13]2[CH2:14][CH2:15][CH2:16][NH:11][CH2:12]2)=[O:18])=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 54435100HCID 54435100, compound

Product 1

HCID 54425483HCID 54425483, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 11.6 g (26.5 mmol) of 3-(2-phenyl-1H-indol-3-ylcarbonyl)piperidine-1-carboxylic acid benzyl ester and 6.4 g (79.5 mmol) of 1,4-cyclohexadiene in ethanol under an atmosphere of nitrogen was charged with 1 g of 10% palladium on carbon. The mixture was heated under reflux for 2 hr, after which it was cooled and filtered to remove the catalyst, and the filtrate evaporated in vacuo to afford 7.5 g (24.7 mmol; 93%) of (2-phenyl-1H-indol-3-yl)piperidin-3-ylmethanone as a clear oil. δH (360 MHz; CDCl3) 1.02-1.15 (1H, m, aliphatic), 1.51-1.70 (2H, m, aliphatics), 1.73-1.84 (2H, m, aliphatics), 2.51-2.62 (1H, m, aliphatic), 2.78-2.89 (3H, m, aliphatics), 2.92-3.02 (1H, m, aliphatic), 7.22-7.28 (2H, m, aromatics), 7.36-7.47 (3H, m, aromatics), 7.50-7.56 (2H, m, aromatics), 8.21-8.27 (1H, m, aromatic), 10.46 (1H, br s, NH); m/z (ES+) 305 (M++H, 100%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hr
  3. temperatureafter which it was cooled
  4. filtrationfiltered
  5. customto remove the catalyst
  6. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-08382672b4384a249cf60972d932fc1b
Source dataset
uspto-grants-2002_11
Patent number
US06479480B1

Reaction notes

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