Acetic Acid → 1-Phenethylamine

HRID 1502927Notes

Reaction equation

HRID 1502927 reaction equation
C([O-])=O.[NH4+:4].[C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=O)[CH3:6].C(O)(=O)C>[Ir].CO>[CH3:6][CH:5]([NH2:4])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 7410AcetophenoneHCID 2723923Ammonium formate

Product 1

HCID 74081-Phenethylamine

Reagents, catalysts & solvents 2

HCID 23924IridiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

946 mg (15.0 mmol) of ammonium formate (MW: 63.06) was introduced in a 20-mL Schlenk tube and subjected to argon-gas replacement. To this, 5 mL of dehydrated methanol, 582 μL (5.0 mmol) of acetophenone (MW: 120.15), 582 μL (5.0 mmol) of acetic acid, and 12.1 mg (0.025 mmol, S/C=200) of the iridium catalyst Ir-1 (MW: 484.01) were added, and the mixture was stirred while heating at 60° C. for 5 hr. After distillation of the solvent, a saturated sodium hydrogen carbonate solution was added, then a product was extracted with methylene chloride, the organic layer was washed with water, and the product was dried with sodium sulfate. The drying agent was removed by filtration and the methylene chloride was distilled away to give a crude product DL-1-phenylethylamine. Its conversion rate was 100% based on NMR measurement, with 92.8% of DL-1-phenylethylamine, 0.4% of 1-phenylethanol, and 6.8% of other by-products.

Workup

  1. distillationAfter distillation of the solvent
  2. additiona saturated sodium hydrogen carbonate solution was added
  3. extractiona product was extracted with methylene chloride
  4. washthe organic layer was washed with water
  5. dry with materialthe product was dried with sodium sulfate
  6. customThe drying agent was removed by filtration
  7. distillationthe methylene chloride was distilled away

Sources & evidence

ORD record
ord-928e35345ade473c85d49030f8aef5ed
Source dataset
uspto-grants-2015_12
Patent number
US09211533B2

Reaction notes

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