2-(4-Dimethylamino-4-phenylcyclohexylidene)-N-[5-(1H-indol-3-yl)pentyl]acetamide hydrochloride → 2-(4-Dimethylamino-4-phenylcyclohexyl)-N-[5-(1H-indol-3-yl)pentyl]-acetamide

HRID 908975Notes

Reaction equation

HRID 908975 reaction equation
Cl.[CH3:2][N:3]([CH3:34])[C:4]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:9][CH2:8][C:7](=[CH:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)=[O:12])[CH2:6][CH2:5]1>[Pd].CO>[CH3:34][N:3]([CH3:2])[C:4]1([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:9][CH2:8][CH:7]([CH2:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)=[O:12])[CH2:6][CH2:5]1

Participants

4

Reactant 1

HCID 116914912-(4-Dimethylamino-4-phenylcyclohexylidene)-N-[5-(1H-indol-3-yl)pentyl]acetamide hydrochloride2×

Product 1

HCID 115911272-(4-Dimethylamino-4-phenylcyclohexyl)-N-[5-(1H-indol-3-yl)pentyl]-acetamideYield 46%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium-on-charcoal (5%, 15 mg) was added to a solution of 2-(4-dimethylamino-4-phenylcyclohexylidene)-N-[5-(1H-indol-3-yl)pentyl]acetamide (base of Example 17; 246 mg, 0.55 mmol) in abs. methanol (30 ml). The reaction mixture was hydrogenated at RT under a pressure of 2 bar for 6 h. The catalyst was separated off over Celite and the filtrate was concentrated. After separation of the residue (234 mg) by chromatography on silica gel (30 g) with EA/methanol (1:1), the product was isolated as a beige-coloured oil in a yield of 46% (112 mg).

Workup

  1. customThe catalyst was separated off over Celite
  2. concentrationthe filtrate was concentrated
  3. customAfter separation of the residue (234 mg) by chromatography on silica gel (30 g) with EA/methanol (1:1)
  4. customthe product was isolated as a beige-coloured oil in a yield of 46% (112 mg)

Sources & evidence

ORD record
ord-d2a29f589b574b359ed9f63ea10d4859
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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