Cl.[Cl:2][C:3]1[CH2:4][CH2:5][NH:6][CH2:7][CH2:8][C:9]=1[C:10]#[N:11].[CH2:12](I)[CH3:13]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:12]([N:6]1[CH2:7][CH2:8][C:9]([C:10]#[N:11])=[C:3]([Cl:2])[CH2:4][CH2:5]1)[CH3:13]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.
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