Octylamine → N-octylpropiolamide

HRID 374274Notes

Reaction equation

HRID 374274 reaction equation
[CH2:1]([NH2:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:10](OC)(=[O:13])[C:11]#[CH:12]>CO>[CH2:1]([NH:9][C:10](=[O:13])[C:11]#[CH:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 8143OctylamineHCID 13536Methyl propiolate

Product 1

HCID 19434623N-octylpropiolamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred, cooled (-30° C.) solution of 18.42 g (0.143 mol) of n-octylamine in 25 ml of aqueous methanol was added 10 g (0.119 mol) of methyl propiolate dropwise. After the addition the reaction mixture was allowed to warm to room temperature and stir for 12 h. The reaction mixture was poured into ice-cold 10% aqueous hydrochloric acid and extracted with dichloromethane. The combined organic layers were washed with saturated aqueous sodium bicarbonate, brine, and dried over magnesium sulfate. Filtration and removal of solvents gave a crude mixture which was purified by column chromatography (Merck 60® silica gel, 25% ethyl acetate/hexane eluant) to give N-octylpropiolamide.

Workup

  1. additionAfter the addition the reaction mixture
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration and removal of solvents
  6. customgave a crude mixture which
  7. customwas purified by column chromatography (Merck 60® silica gel, 25% ethyl acetate/hexane eluant)

Sources & evidence

ORD record
ord-edb205b503b44e3f963aabc674ddc970
Source dataset
uspto-grants-1992_11
Patent number
US05166390

Reaction notes

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