HCID 66783146, compound → HCID 24955428, compound

HRID 1095559Notes

Reaction equation

HRID 1095559 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

HCID 66783146HCID 66783146, compound

Product 1

HCID 24955428HCID 24955428, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

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.

Workup

  1. filtrationThe catalyst was then filtered off with suction over Celite
  2. concentrationthe filtrate was concentrated
  3. customThe 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)]

Sources & evidence

ORD record
ord-d160c1ae519645e1b39eefc3d4bd5c4e
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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