Iodoethane → 1-Ethyl-4-chloro-5-cyano-2,3,6,7-tetrahydro-1H-azepine

Participants

Reaction Steps

7.1 gm (0.037 mol) of 4-chloro-5-cyano-2,3,6,7-tetrahydro-1H-azepine hydrochloride were dissolved in 170 ml of chloroform by addition of 28.5 ml of triethylamine. Then, 8.6 gm (0.055 mol)=4.9 ml of ethyl iodide were added dropwise at the boiling point, while stirring, and the mixture was refluxed for 4 hours. To complete the reaction, another 10 ml of triethylamine and 2.5 ml of ethyl iodide were added, and the mixture was boiled further. After a total of 10 hours the reaction was finished. After standing overnight, the mixture was concentrated by evaporation in vacuo. The residue was chromatographed on a silica-gel column (chloroform/methyl alcohol/ammonia=9:1:0.1). After the corresponding fractions had been concentrated by evaporation, the mixture was evaporated in vacuo.

Provenance & Evidence