HCID 11712509, compound → 2-[4-dimethylamino-4-(3-fluorophenyl)cyclohexyl]-N-[2-(1H-indol-3-yl)-1-methylethyl]acetamide

HRID 908989Notes

Reaction equation

HRID 908989 reaction equation
[CH3:1][N:2]([CH3:32])[C:3]1([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)[CH2:8][CH2:7][C:6](=[CH:9][C:10]([NH:12][CH:13]([CH3:24])[CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)=[O:11])[CH2:5][CH2:4]1>[Pd].CO>[CH3:32][N:2]([CH3:1])[C:3]1([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([NH:12][CH:13]([CH3:24])[CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)=[O:11])[CH2:5][CH2:4]1

Participants

4

Reactant 1

HCID 11712509HCID 11712509, compound

Product 1

HCID 116485072-[4-dimethylamino-4-(3-fluorophenyl)cyclohexyl]-N-[2-(1H-indol-3-yl)-1-methylethyl]acetamideYield 4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium-on-charcoal (5%, 40 mg) was added to a solution of 2-[4-dimethylamino-4-(3-fluorophenyl)-cyclohexylidene]-N-[2-(1H-indol-3-yl)-1-methylethyl]-acetamide (417 mg, 0.96 mmol) in abs. methanol (40 ml). The reaction mixture was hydrogenated at RT under a pressure of 3 bar for 15 h. The catalyst was separated off over Celite and the filtrate was concentrated. After separation of the residue by chromatography on silica gel G [50 g; EA/MeOH (10:1)-(5:1)], the less polar diastereoisomer of 2-[4-dimethylamino-4-(3-fluorophenyl)cyclohexyl]-N-[2-(1H-indol-3-yl)-1-methylethyl]acetamide was isolated in a yield of 4% (15 mg) and the more polar diastereoisomer of 2-[4-dimethylamino-4-(3-fluorophenyl)cyclohexyl]-N-[2-(1H-indol-3-yl)-1-methylethyl]acetamide was isolated in a yield of 41% (170.2 mg). Both products were colourless oils and diastereoisomerically pure.

Workup

  1. customThe catalyst was separated off over Celite
  2. concentrationthe filtrate was concentrated
  3. customAfter separation of the residue by chromatography on silica gel G [50 g; EA/MeOH (10:1)-(5:1)]

Sources & evidence

ORD record
ord-80285d76b2df42b19620f6d442233c2e
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

Loading…