Hydrochloric Acid → Benzenemethanamine, N-ethyl-4-(trifluoromethyl)-

HRID 898905Notes

Reaction equation

HRID 898905 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6]([CH2:7][NH:8][C:9](=O)[CH3:10])=[CH:5][CH:4]=1.B.CSC.Cl>C1COCC1>[F:1][C:2]([F:14])([F:15])[C:3]1[CH:13]=[CH:12][C:6]([CH2:7][NH:8][CH2:9][CH3:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12423031(Dimethyl sulfide)trihydroboronHCID 23132710N-[4-(trifluoromethyl)benzyl]acetamide

Product 1

HCID 485421Benzenemethanamine, N-ethyl-4-(trifluoromethyl)-Yield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-[4-(trifluoromethyl)benzyl]acetamide (3.085 g, 14.204 mmol) was dissolved in THF (100 ml) and was cooled to zero degrees under argon atmosphere. (Methylthio)methane compound with borane (1:1) (2.698 g, 35.511 mmol) was added and the mixture was refluxed over night at RT. HCl (15 ml, 10%) was gently added and was stirred overnight. The solvent was removed by evaporation Diethyl ether (20 ml) was added and the product was extracted to the water phase by K2CO3 (3×15 ml), the water phase was acidified by HCl (10 ml, 10%) and the product was extracted to the organic phase by EtOAc (3×15 ml). The organic phase was dried (MgSO4) and the solvent was removed by evaporation to give 0.809 g of N-[4-(trifluoromethyl)benzyl]ethanamine (yield 28%).

Workup

  1. temperaturewas cooled to zero degrees under argon atmosphere
  2. customThe solvent was removed by evaporation Diethyl ether (20 ml)
  3. additionwas added
  4. extractionthe product was extracted to the water phase by K2CO3 (3×15 ml)
  5. extractionthe product was extracted to the organic phase by EtOAc (3×15 ml)
  6. dry with materialThe organic phase was dried (MgSO4)
  7. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-29b878b89e1047aca938bc0962bff8ca
Source dataset
uspto-grants-2008_04
Patent number
US07351858B2

Reaction notes

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