Collect. Czech. Chem. Commun. 1983, 48, 1898-1909

11-(Dimethylaminoalkyl)-6,11-dihydrodibenzo[b,e]thiepin-11-carbonitriles and some related compounds

Karel Šindelář, Jiří Holubek, Miroslav Ryska, Emil Svátek, Jiří Urban and Miroslav Protiva

Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3


The title compounds II and III were obtained by alkylations of 6,11-dihydrodibenzo[b,e]thiepin-11-carbonitrile (I) with 2-dimethylaminoethyl chloride and 3-dimethylaminopropyl chloride in the presence of sodium hydride or sodium amide. Hydrolysis of the nitrile II with potassium hydroxide in ethanol resulted in a small amount of the amino acid X and in the amine XI as the main product. Alkylations of I with 1,2-dibromoethane and 1,3-dibromopropane in the presence of sodium hydride gave the bromoalkylnitriles IV and V and the alkylenebisnitriles XIII and XIV. The preparation of the methylpiperazinopropyl derivative VI proved the usefulness of compounds IV and V in the synthesis of further aminonitriles of this series. Alkylation of the nitrile I with 1,2-dibromoethane in the presence of sodium hydroxide or potassium carbonate and benzyltriethylammonium chloride afforded three isomeric nitriles C17H13NS: the vinyl derivative IX, the 6,11-ethano-6H, 11H-dibenzo[b,e]thiepin derivative XV and finally the 1a,11b-dihydro-1H,7H-dibenzo[b,f]cyclopropa[d]thiocin derivative XVI. Compounds II, III, VI and XII showed some spasmolytic effects but their central neurotropic activity is insignificant.