Potassium Carbonate → HCID 86638575, compound

HRID 1807786Notes

Reaction equation

HRID 1807786 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([OH:33])([C:29]([F:32])([F:31])[F:30])[C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:26][C:25]([F:27])([F:28])[C:24]([C:21]1[CH:22]=[CH:23][C:18]([CH2:17][N:13]2[CH2:14][CH2:15][N:10]([C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=3)[CH2:11][CH2:12]2)=[CH:19][CH:20]=1)([OH:33])[C:29]([F:30])([F:32])[F:31]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 804471-(4-Nitrophenyl)piperazineHCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 86638575HCID 86638575, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(4-nitrophenyl)piperazine (19.30 mmol, 4 g), 2-(4-(bromomethyl)-phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (19.30 mmol, 6.51 g) and potassium carbonate (19.30 mmol, 2.67 g) in acetonitrile (10 mL) was refluxed for 20 hours and was then concentrated under reduced pressure. Dichloromethane was added and the insolubles were filtered off. The filtrate was chromatographed on silica eluting with a gradient of dichloromethane to dichloromethane/ethyl acetate (10%) to give the title compound (8 g).

Workup

  1. temperaturewas refluxed for 20 hours
  2. concentrationwas then concentrated under reduced pressure
  3. additionDichloromethane was added
  4. filtrationthe insolubles were filtered off
  5. customThe filtrate was chromatographed on silica eluting with a gradient of dichloromethane to dichloromethane/ethyl acetate (10%)

Sources & evidence

ORD record
ord-c900da146fe74038afd5cf89f13cec5d
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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