HCID 66783146, compound → HCID 24955428, compound
Reaction equation
[CH2:1]([C:5]1([N:26]([CH3:28])[CH3:27])[CH2:10][CH2:9][C:8]([C:11]2[NH:12][C:13]3[C:18]([C:19]=2[CH3:20])=[CH:17][C:16]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:15][CH:14]=3)=[CH:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]>C(O)C.[Pd]>[CH2:1]([C:5]1([N:26]([CH3:28])[CH3:27])[CH2:6][CH2:7][CH:8]([C:11]2[NH:12][C:13]3[C:18]([C:19]=2[CH3:20])=[CH:17][C:16]([O:21][C:22]([F:25])([F:23])[F:24])=[CH:15][CH:14]=3)[CH2:9][CH2:10]1)[CH2:2][CH2:3][CH3:4]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
(±)-N-[1-Butyl-4-(3-methyl-5-trifluoromethoxy-1H-indol-2-yl)cyclohex-3-enyl]-N,N-dimethylamine (320 mg, 0.81 mmol) was dissolved in ethanol (50 ml), and Pd/C (5%, 140 mg) was added under argon. Hydrogenation was carried out under 3 bar for 1.5 h. The catalyst was then filtered off with suction over Celite and the filtrate was concentrated. The solid pale brown residue (341 mg) was separated by chromatography [silica gel 60 (30 g); ethyl acetate/methanol (1:1; 500 ml); (1:2; 300 ml)]. 1-Butyl-N,N-dimethyl-4-(3-methyl-5-(trifluoromethoxy)-1H-indol-2-yl)cyclohexanamine (less polar diastereoisomer) was obtained in a yield of 28 mg (9%) and the more polar diastereoisomer in a yield of 237 mg (75%), in each case as a colourless solid.