N-(2-aminoethyl)acetamide → HCID 19095305, compound

Participants

Reaction Steps

3-(1,3-Dioxolan-2-yl)-2-methylpropiophenone (7.1 g) was added to a solution of 6.6 g of N-acetylethylenediamine in 100 ml of acetic acid under argon and while stirring. The reaction solution was boiled for 18 hours and the acetic acid was subsequently removed in a vacuum. The residue was taken up in 200 ml of methylene chloride and washed with a mixture of 100 ml of saturated sodium hydrogen carbonate solution and 160 ml of 2N sodium hydroxide solution. The aqueous phase was back-extracted twice with 100 ml of methylene chloride each time. The organic phases were combined, dried with MgSO4 and freed from solvent. The residue, 7.6 g of brown oil was chromatographed on 350 g of silica gel with ethyl acetate/hexane mixtures (1:3 to 2:1) as the eluent. 4.6 g (59%) of N-[2-[3-methyl-2-phenylpyrrol-1-yl]ethyl]acetamide were isolated as a brown, amorphous solid. MS: m/e=242 (M+ ).

Provenance & Evidence