Attempts at C-alkylation of 2, 3-dihydro-4H-l-benzothiepin-5-one (1) reached their goal only if the starting compound was activated by a form of 4-ethoxycarbonyl derivative (II) or pyrrolidine enamine (V); compounds III and IV were obtained in low yields. Using 8 steps, compound XVI was synthesized from ketone I. C-Alkylation of 5-phenyl-2, 3, 4, 5-tetrahydro-l- benzothiepin (XVIII) led to a low yield of 5-(3-dimethylaminopropyl) derivative XIX. ...