N-(2-aminoethyl)acetamide → HCID 19095285, compound

Participants

Reaction Steps

3',4'-Dichloro-3-(1,3-dioxolan-2-yl)propiophenone (10.0 g) was dissolved in 20 ml of acetic acid and added under argon and while stirring to a solution of 7.4 g of N-acetylethylenediamine in 80 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 200 ml of methylene chloride and washed with a mixture of 100 ml of saturated sodium hydrogen carbonate solution and 100 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, 12.5 g of dark brown oil were chromatographed on 500 g of silica gel with ethyl acetate as the eluent. 9.1 g (84%) of N-[2-[2-(3,4-dichlorophenyl)-pyrrol-1-yl]ethyl]acetamide were isolated as a yellow-brown oil. MS: m/e=296, 298, 300 (9:6:1, M+).

Provenance & Evidence