N-(2-aminoethyl)acetamide → HCID 19095412, compound

Participants

Reaction Steps

3-(1,3-Dioxolan-2-yl)-3',4'-dimethoxypropiophenone (6.3 g) was dissolved in 30 ml of acetic acid and added under argon and while stirring to a solution of 4.9 g of N-acetylethylenediamine in 50 ml of acetic acid. The reaction mixture was heated to reflux overnight, the acetic acid was subsequently removed in a vacuum. The residue was taken up in 150 ml of methylene chloride and washed with a mixture of 100 ml of saturated sodium hydrogen carbonate solution and 150 ml of 2N sodium hydroxide solution. The aqueous phase was back-extracted three times with 100 ml of methylene chloride each time, the organic phases were combined, dried with MgSO4 and freed from solvent. The residue, 7.3 g of dark brown oil, was chromatographed on 250 g of silica gel with ethyl acetate as the eluent. 2.6 g (38%) of N-[2-[2-(3,4-dimethoxyphenyl)pyrrol-1-yl]-ethyl]acetamide were isolated as a brown oil.

Provenance & Evidence