alpha-(Trifluoromethyl)benzenemethanamine → (alphaR)-alpha-(Trifluoromethyl)benzenemethanamine

HRID 245143Notes

Reaction equation

HRID 245143 reaction equation
C(O)(=O)[C@@H]([C@H](C(O)=O)O)O.[F:11][C:12]([F:22])([F:21])[CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH2:14]>C(O)(C)C>[F:11][C:12]([F:21])([F:22])[C@@H:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH2:14]

Participants

4

Reactant 2

HCID 89166alpha-(Trifluoromethyl)benzenemethanamineHCID 444305L-Tartaric acid

Product 1

HCID 11789718(alphaR)-alpha-(Trifluoromethyl)benzenemethanamineYield 31.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

L-Tartaric acid (36 g, 240.0 mmol) was added to a solution of 2,2,2-trifluoro-1-phenylethanamine (40 g, 228.57 mmol) in isopropanol (400 mL). The solution was heated to reflux for 30 min. The mixture was cooled and the solid was collected by filtration. The material was diluted with Na2CO3/H2O and the aqueous mixture was extracted with methylene chloride (3×100 mL). The combined organic extracts were dried over K2CO3 and concentrated under reduced pressure to afford (1R)-2,2,2-trifluoro-1-phenylethanamine (12.5 g, 31% yield) as a white solid.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 30 min
  3. temperatureThe mixture was cooled
  4. filtrationthe solid was collected by filtration
  5. additionThe material was diluted with Na2CO3/H2O
  6. extractionthe aqueous mixture was extracted with methylene chloride (3×100 mL)
  7. dry with materialThe combined organic extracts were dried over K2CO3
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-79dc0351029842de8514c9bcae18f474
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

Loading…