2-(4-dimethylamino-4-phenylcyclohexylidene)-1-[3-(1H-indol-3-yl)piperidine-1-yl]-ethanone → 2-(4-dimethylamino-4-phenylcyclohexyl)-1-[3-(1H-indol-3-yl)piperidine-1-yl]-ethanone

HRID 2357489Notes

Reaction equation

HRID 2357489 reaction equation
[CH3:1][N:2]([CH3:33])[C:3]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:8][CH2:7][C:6](=[CH:9][C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH:14]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[NH:20][CH:19]=3)[CH2:13]2)=[O:11])[CH2:5][CH2:4]1>[Pd].CO>[CH3:33][N:2]([CH3:1])[C:3]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH:14]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[NH:20][CH:19]=3)[CH2:13]2)=[O:11])[CH2:5][CH2:4]1

Participants

4

Reactant 1

HCID 99567182-(4-dimethylamino-4-phenylcyclohexylidene)-1-[3-(1H-indol-3-yl)piperidine-1-yl]-ethanone

Product 1

HCID 99825912-(4-dimethylamino-4-phenylcyclohexyl)-1-[3-(1H-indol-3-yl)piperidine-1-yl]-ethanoneYield 30%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on carbon (5%, 60 mg) was added to a solution of 2-(4-dimethylamino-4-phenylcyclohexylidene)-1-[3-(1H-indol-3-yl)piperidine-1-yl]-ethanone (220 mg, 0.498 mmole) in abs. methanol (30 ml). The reaction mixture was hydrogenated for 24 hours at RT under a pressure of 3 bar. The catalyst was separated using Celite and the filtrate was concentrated by evaporation. After chromatographic separation of the residue (210 mg) on silica gel (20 g) with EE/methanol (2:1), 2-(4-dimethylamino-4-phenylcyclohexyl)-1-[3-(1H-indol-3-yl)piperidine-1-yl]-ethanone was isolated as a colourless oil in a yield of 30% (66 mg). The compound was obtained as a diastereoisomer mixture.

Workup

  1. customThe catalyst was separated
  2. concentrationthe filtrate was concentrated by evaporation
  3. customAfter chromatographic separation of the residue (210 mg) on silica gel (20 g) with EE/methanol (2:1)

Sources & evidence

ORD record
ord-9cb181c25fcf4aa192e0fdc5ccdafda9
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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