Potassium Carbonate → 1,1,1,3,3,3-Hexafluoro-2-(4-((4-(4-nitrobenzylidene)piperidin-1-yl)methyl)phenyl)propan-2-ol

HRID 515279Notes

Reaction equation

HRID 515279 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH:8]=[C:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]([OH:40])([C:36]([F:39])([F:38])[F:37])[C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=1>C(#N)C>[F:33][C:32]([F:34])([F:35])[C:31]([C:28]1[CH:29]=[CH:30][C:25]([CH2:24][N:12]2[CH2:11][CH2:10][C:9](=[CH:8][C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:16][CH:15]=3)[CH2:14][CH2:13]2)=[CH:26][CH:27]=1)([OH:40])[C:36]([F:37])([F:39])[F:38]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-olHCID 67194164HCID 67194164, compound

Product 1

HCID 866709361,1,1,3,3,3-Hexafluoro-2-(4-((4-(4-nitrobenzylidene)piperidin-1-yl)methyl)phenyl)propan-2-olYield 64.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a stirred mixture of 4-(4-nitrobenzylidene)piperidine (23.83 mmol, 5.2 g) and potassium carbonate (31.0 mmol, 4.28 g) in acetonitrile was added a solution of 2-(4-(bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (23.83 mmol, 8.03 g) in acetonitrile. The reaction was stirred for 5 hours then was concentrated under reduced pressure. Dichloromethane was added and the reaction was filtered. The filtrate was chromatographed on silica (eluting with a gradient of dichloromethane to dichloromethane/ethyl acetate) to give the title compound (7.3 g).

Workup

  1. concentrationthen was concentrated under reduced pressure
  2. additionDichloromethane was added
  3. filtrationthe reaction was filtered
  4. customThe filtrate was chromatographed on silica (
  5. washeluting with a gradient of dichloromethane to dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-e8d41c0a48d644ea9543f9f9bf56fdfd
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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