Potassium Permanganate → HCID 88919654, compound

HRID 2206924Notes

Reaction equation

HRID 2206924 reaction equation
[F:1][C:2]([F:39])([F:38])[C:3]1[CH:4]=[C:5]([C:13]2([C:34]([F:37])([F:36])[F:35])[CH2:17][CH2:16][N:15]([C:18]3[N:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[C:21]([CH2:28][NH:29][C:30](=[O:33])[CH2:31][CH3:32])=[CH:20][CH:19]=3)[CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[Mn]([O-])(=O)(=O)=[O:41].[K+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl>[F:39][C:2]([F:1])([F:38])[C:3]1[CH:4]=[C:5]([C:13]2([C:34]([F:35])([F:36])[F:37])[CH2:14][N:15]([C:18]3[N:23]=[C:22]([C:24]([F:25])([F:27])[F:26])[C:21]([CH2:28][NH:29][C:30](=[O:33])[CH2:31][CH3:32])=[CH:20][CH:19]=3)[C:16](=[O:41])[CH2:17]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 87158696HCID 87158696, compound

Product 1

HCID 88919654HCID 88919654, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

N-{[6-{3-[3,5-Bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-1-yl}-2-(trifluoro-methyl)pyridin-3-yl]methyl}propanamide (0.3 g), benzyltriethylammonium chloride (0.35 g) and potassium permanganate (0.25 g) were added to dichloromethane (20 ml), and the mixture was stirred for 75 hours at room temperature. Upon the completion of the stirring, the reaction mixture was filtered through a short silica gel layer to remove precipitate. The filtrate was distilled off under reduced pressure and the purification was carried out by silica gel column chromatography to obtain N-{[6-{4-[3,5-bis(trifluoromethyl)phenyl]-2-oxo-4-(trifluoromethyl)pyrrolidin-1-yl}-2-(trifluoromethyl)pyridin-3-yl]methyl}propanamide (0.08 g).

Workup

  1. filtrationUpon the completion of the stirring, the reaction mixture was filtered through a short silica gel layer
  2. customto remove precipitate
  3. distillationThe filtrate was distilled off under reduced pressure
  4. customthe purification

Sources & evidence

ORD record
ord-34692ced41b84d47a755a0a3acbd9ead
Source dataset
uspto-grants-2016_06
Patent number
US09375000B2

Reaction notes

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