Phenethylamine → Formamide, N-(2-phenylethyl)-

HRID 1405517Notes

Reaction equation

HRID 1405517 reaction equation
[C:1]1([CH2:7][CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:10](OCC)=[O:11]>>[CH2:8]([NH:9][CH:10]=[O:11])[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 1001PhenethylamineHCID 8025Ethyl formate

Product 1

HCID 140995Formamide, N-(2-phenylethyl)-

Procedure

Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 2-phenylethanamine (1.9 g, 15.70 mmol, 1.00 equiv). This was followed by the addition of ethyl formate (5 g, 67.57 mmol, 4.30 equiv) dropwise with stirring. The resulting solution was stirred overnight at 50° C. The resulting solution was concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (70:1). This resulted in 2.27 g (97%) of N-phenethylformamide as yellow oil.

Workup

  1. customInto a 100-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. stirringThe resulting solution was stirred overnight at 50° C
  4. concentrationThe resulting solution was concentrated under vacuum
  5. customThis resulted in 2.27 g (97%) of N-phenethylformamide as yellow oil

Sources & evidence

ORD record
ord-6f09542f29b44708baaf483aca91b093
Source dataset
uspto-grants-2014_12
Patent number
US08916560B2

Reaction notes

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