Chlorpromazine (Ⅰ) produces depression of the central nervous system.It also exhibits weak adrenolytic and hypotensive effects.Hexahydro-l-azepinylpropionamidoxime (Ⅱ) and guanethidine (Ⅲ) were reported to have protracted antihypertensive properties with the capacity to block the transmission at peripheral adrenergic nerve terminals.The present work deals with the structural hybridization of chlorpromazine with hexahydro-1-azepinvl-nropionamidoxime and Quanethidine.The 2-chloro-l0-aminoacylphenothiazines(Ⅳ) were prepared by condensation of the appropriate 2-chloro-l0-haloacylphenothiazines or 2-chloro-l0-methacrylylphenothiazine and amines.2-Chlorophenothiazine was condensed with 1-(β-chloroethyl)heptamethy-lenimine in the presence of sodium amide,giving 2-chloro-10-[β-(N-heptamethylenimino) ethyl] phenothiazine (Va).β-[10-Phenothiazinyl) propionic acid (Ⅵa) and methyl β-(10-(2-chlorophenothiazinyl)] propionate (Ⅵc) reacted with hexamethylenimine or heptamethylenimine in the presence of lithium aluminium hydride in boiling tetrahydrofuran,forming the corresponding 10-(γ-aminopropyl)phenothiazines (Ⅴb,Ⅴc).We attempted to prepare β-[10-(2-chlorophenothiazinyl)] propionyl chloride,but only 10-chloro-2,3-dihydro-3-keto-lH-pyrido[3,2,1-k1]phenothiazine (Ⅶa) was obtained.Ⅶa was treated with paraformaldehyde and hexamethylenimine hydrochloride in isopropyl alcohol,giving the desired Mannich base (Ⅶd).The reduction of 1 (β-chloropropionyl) hexamethylenimine (Ⅹ) by means of lithium aluminium hydride yielded 1-propylhexamethylenimine (ⅩⅠ)