Water → (4,4,5,5,5-Pentafluoropentyl)benzylamine

HRID 1792355Notes

Reaction equation

HRID 1792355 reaction equation
[F:1][C:2]([F:22])([C:18]([F:21])([F:20])[F:19])[CH2:3][CH2:4][CH2:5]OC1C=CC=C(C)C=1S([O-])(=O)=O.[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[F:1][C:2]([F:22])([C:18]([F:21])([F:20])[F:19])[CH2:3][CH2:4][CH2:5][NH:30][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 867560744,4,5,5,5-Pentafluoropentyloxytoluenesulfonate

Product 1

HCID 18770251(4,4,5,5,5-Pentafluoropentyl)benzylamineYield 74%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4,4,5,5,5-Pentafluoropentyloxytoluenesulfonate (1 g, 3 mmol) was dissolved in acetonitrile (10 ml). Benzylamine (646 mg, 6 mmol) and potassium carbonate (829 mg, 6 mmol) were added. The mixture was refluxed for 10 h under nitrogen atmosphere. When the reaction was completed, the mixture was cooled to room temperature. Water was added to reaction solution which was then extracted with ethyl acetate. The extracted organic layer was dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to column chromatography (dichloromethane:ethyl acetate=19:1) to give 590 mg (yield: 74%) of the title compound as a pale yellow liquid.

Workup

  1. temperatureThe mixture was refluxed for 10 h under nitrogen atmosphere
  2. extractionwas then extracted with ethyl acetate
  3. dry with materialThe extracted organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-05194e24a7d94b56b66c94a62f3f92e7
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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