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
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]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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).