HCID 66783085, compound → HCID 24955426, compound

HRID 1095558Notes

Reaction equation

HRID 1095558 reaction equation
[CH2:1]([C:8]1([N:29]([CH3:31])[CH3:30])[CH2:13][CH2:12][C:11]([C:14]2[NH:15][C:16]3[C:21]([C:22]=2[CH3:23])=[CH:20][C:19]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:18][CH:17]=3)=[CH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.C(O)C.[Pd]>[CH2:1]([C:8]1([N:29]([CH3:31])[CH3:30])[CH2:9][CH2:10][CH:11]([C:14]2[NH:15][C:16]3[C:21]([C:22]=2[CH3:23])=[CH:20][C:19]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:18][CH:17]=3)[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 66783085HCID 66783085, compound

Product 1

HCID 24955426HCID 24955426, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

(±)-N-[1-Benzyl-4-(3-methyl-5-trifluoromethoxy-1H-indol-2-yl)cyclohex-3-enyl]-N,N-dimethylamine (230 mg, 0.53 mmol) was dissolved in methanol (40 ml) and ethanol (10 ml), while heating, and Pd/C (5%, 100 mg) was added under argon. Hydrogenation was carried out at 40° C. under 3 bar for 4 h. The catalyst was then filtered off with suction over Celite and the filtrate was concentrated. The solid colourless residue (227 mg) was separated by chromatography [silica gel 60 (30 g); ethyl acetate/methanol (20:1; 400 ml); (4:1; 500 ml) (2:1; 300 ml)]. 1-Benzyl-N,N-dimethyl-4-(3-methyl-5-(trifluoromethoxy)-1H-indol-2-yl)cyclohexanamine (more polar diastereomer) was obtained in a yield of 175 mg (77%) as a colourless solid.

Workup

  1. filtrationThe catalyst was then filtered off with suction over Celite
  2. concentrationthe filtrate was concentrated
  3. customThe solid colourless residue (227 mg) was separated by chromatography [silica gel 60 (30 g); ethyl acetate/methanol (20:1; 400 ml); (4:1; 500 ml) (2:1; 300 ml)]

Sources & evidence

ORD record
ord-9cddef26f72742748ee28bac17e993f7
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

Loading…