Formic Acid → 3-Phenylpropylformamide

HRID 366117Notes

Reaction equation

HRID 366117 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:11](O)=[O:12].C(OC(=O)C)(=O)C>O>[C:1]1([CH2:7][CH2:8][CH2:9][NH:10][CH:11]=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Procedure

3-Phenylproylamine (10 ml, 70.0 mmol) was added at 0° C. dropwise to formic acid (80 ml). Acetic acid anhydride (30 ml) was added dropwise to the reaction mixture. After the addition the reaction mixture was warmed to room temperature. It was stirred for 2.5 h. It was cooled to 0° C. Water (30 ml) was added dropwise. The reaction mixture was warmed to room temperature. The solvent was removed in vacuo. The residue was dissolved in ethyl acetate (300 ml). The organic phase was washed with saturated sodium chloride solution (2×150 ml) and with saturated sodium hydrogen carbonate solution (200 ml). It was dried over magnesium sulfate. The solvent was removed in vacuo to furnish 5.82 g of N-(3-phenylpropyl)formamide, which was used without further purification.

Workup

  1. additionAfter the addition the reaction mixture
  2. temperatureIt was cooled to 0° C
  3. temperatureThe reaction mixture was warmed to room temperature
  4. customThe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate (300 ml)
  6. washThe organic phase was washed with saturated sodium chloride solution (2×150 ml) and with saturated sodium hydrogen carbonate solution (200 ml)
  7. dry with materialIt was dried over magnesium sulfate
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-adc96d2e80264701ba4abb0602a89d37
Source dataset
uspto-grants-2000_10
Patent number
US06127354

Reaction notes

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