N-(2-aminoethyl)acetamide → Acetamide,n-[2-[2-[4-(trifluoromethyl)phenyl]-1h-pyrrol-1-yl]ethyl]-

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Reaction Steps

3-(1,3-Dioxolan-2-yl)-4'-(trifluoromethyl)-propiophenone (6.4 g) was added under argon and while stirring to a solution of 4.8 g of N-acetylethylenediamine in 70 ml of acetic acid. The reaction mixture was refluxed 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 70 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, 9.4 g of yellow-brown solid was chromatographed on 500 g of silica gel with ethyl acetate as the eluent. 5.4 g (78%) of N-[2-[2-[4-(trifluoromethyl)phenyl]-pyrrol-1-yl]ethyl]acetamide were isolated as a yellow amorphous solid. MS: m/e=296 (M+).

Provenance & Evidence