Phenethylamine → 2,2,2-Trifluoro-N-(2-phenylethyl)ethan-1-amine

HRID 1640238Notes

Reaction equation

HRID 1640238 reaction equation
[F:1][C:2]([F:13])([F:12])[CH2:3]OS(C(F)(F)F)(=O)=O.[CH2:14]([NH2:22])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C(C)=CC=CC=1>[CH2:14]([NH:22][CH2:3][C:2]([F:13])([F:12])[F:1])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 1001PhenethylamineHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonate

Product 1

HCID 135556072,2,2-Trifluoro-N-(2-phenylethyl)ethan-1-amine

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

1.9 g (8.3 mmol) 2,2,2-trifluoroethyltrifluoromethanesulphonate were added to 2.0 g (16.5 mmol) phenethylamine in 50 mL xylene and the reaction mixture was refluxed overnight. After cooling the precipitate formed was suction filtered, washed with DIPE and the filtrate washed evaporated down i.vac. The residue was purified by flash chromatography. The product fractions were combined and evaporated down i.vac.

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. temperatureAfter cooling the precipitate
  3. customformed
  4. filtrationfiltered
  5. washwashed with DIPE
  6. washthe filtrate washed
  7. customevaporated down i.vac
  8. customThe residue was purified by flash chromatography
  9. customevaporated down i.vac

Sources & evidence

ORD record
ord-3b6f770e15b4411da73f674d6141b332
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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