HCID 66782806, compound → HCID 24953645, compound

HRID 1095555Notes

Reaction equation

HRID 1095555 reaction equation
[CH2:1]([C:8]1([N:28]([CH3:30])[CH3:29])[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]([C:24]([F:27])([F:26])[F:25])=[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.[Pd]>[CH2:1]([C:8]1([N:28]([CH3:30])[CH3:29])[CH2:13][CH2:12][CH:11]([C:14]2[NH:15][C:16]3[C:21]([C:22]=2[CH3:23])=[CH:20][C:19]([C:24]([F:26])([F:27])[F:25])=[CH:18][CH:17]=3)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 66782806HCID 66782806, compound

Product 1

HCID 24953645HCID 24953645, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(±)-[1-Benzyl-4-(3-methyl-5-trifluoromethyl-1H-indol-2-yl)cyclohex-3-enyl]-dimethylamine (220 mg, 0.53 mmol) was dissolved in methanol (50 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 was separated by chromatography [silica gel 60 (30 g); ethyl acetate/methanol (20:1; 500 ml); (4:1; 300 ml); (2:1; 300 ml)]. N-[1-Benzyl-4-(3-methyl-5-trifluoromethyl-1H-indol-2-yl)cyclohexyl]-N,N-dimethylamine (less polar diastereoisomer) was isolated in a yield of 46 mg (21%) as a colourless solid with a melting point of 180-210° C. The polar diastereoisomer was obtained in a yield of 152 mg (69%) as a colourless solid with a melting point of 166-174° C.

Workup

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

Sources & evidence

ORD record
ord-e77185dc77f64abf9d5f27cd174a4f47
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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