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

HRID 908973Notes

Reaction equation

HRID 908973 reaction equation
Cl.[CH3:2][N:3]([CH3:32])[C:4]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:9][CH2:8][C:7](=[CH:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)=[O:12])[CH2:6][CH2:5]1>[Pd].CO>[CH3:32][N:3]([CH3:2])[C:4]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:9][CH2:8][CH:7]([CH2:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)=[O:12])[CH2:6][CH2:5]1

Participants

4

Reactant 1

HCID 116553562-(4-Dimethylamino-4-phenylcyclohexylidene)-N-[3-(1H-indol-3-yl)propyl]acetamide hydrochloride2×

Product 1

HCID 115833142-(4-Dimethylamino-4-phenylcyclohexyl)-N-[3-(1H-indol-3-yl)propyl]-acetamideYield 29%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium-on-charcoal (5%, 20 mg) was added to a solution of 2-(4-dimethylamino-4-phenyl-cyclohexylidene)-N-[3-(1H-indol-3-yl)propyl]-acetamide (base of Example 16; 305 mg, 0.734 mmol) in abs. methanol (30 ml). The reaction mixture was hydrogenated at RT under a pressure of 3 bar for 6 h. The catalyst was separated off over Celite and the filtrate was concentrated. After separation of the residue (289 mg) by chromatography on silica gel (20 g) with EA/methanol (2:1), the product was isolated as a beige-coloured oil in a yield of 29% (95 mg).

Workup

  1. customThe catalyst was separated off over Celite
  2. concentrationthe filtrate was concentrated
  3. customAfter separation of the residue (289 mg) by chromatography on silica gel (20 g) with EA/methanol (2:1)
  4. customthe product was isolated as a beige-coloured oil in a yield of 29% (95 mg)

Sources & evidence

ORD record
ord-e670d0387b01441fa8879124f44e8433
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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