Patent GB-1125929-A (GB)
Title: New tricyclic amines their production and use
IPC: C07D295/04
Filed: 1966-08-11
Abstract: 1,125,929. Dibenzocycloheptene derivatives. J. R. GEIGY A.G. 11 Aug., 1966 [12 Aug., 1965; 19 Aug., 1965], No. 35956/66. Heading C2C. [Also in Divisions A5 and C5] The invention comprises compounds of the Formula I, whereinX and Y represent hydrogen, chlorine or bromine atoms, or C 1-3  alkyl or C 1-3  alkoxy groups; Z represents a hydrogen, chlorine or bromine atom or an C 1-3  alkyl or C 1-3  alkoxy group or, when X and Y represent hydrogen atoms Z 1  may represent an C 1-2  alkylthio group; R 1  represents an C 1-4  alkyl group or a hydrogen atom; R 2  represents a hydrogen atom or a methyl group and R 3  and R 4  represent hydrogen atoms or C 1-4  alkyl groups or -NR 3 R 4  represents a saturated heterocyclic radical of 5 to 7 ring members having optionally, as a ring member, an imino, an C 1-5  alkylimino, a C 1-5  hydroxyalkylimino or an C 2-8  alkanoyloxyalkylimino group and their acid addition salts and their preparation by reacting a reactive ester of an alcohol of the Formula II with a compound of the formula HNR 3 R 4  with an N-acyl derivative of piperazine or hexo-hydro-1H-1,4-diazepine or with a metal derivative of an N-acyl derivative of a C 1-4  alkylamine and if necessary, subjecting the reaction product to hydrolysis to split off any acyl radical bound to a nitrogen atom in the side chain and, if desired, reacting a resulting compound having an imino group as ring member with an alkylene oxide of up to 5 carbon atoms, with a reactive-monoester of an C 1-5  alkane diol or a reactive ester of an C 2-8  alkanoyloxy alkanol and, if desired, acylating a compound of the Formula I containing a C 1-5  hydroxyalkylimino group into a compound having an C 2-8  alkanoyloxy alkylimino group and, if desired, converting a resulting compound into an acid addition salt thereof. H - (5H - dibenzo[a, d]cyclohepten-10-ylmethyl) piperazine - 1 - carboxylic acid ethyl ester may be prepared by reacting ethyl piperazine-1- carboxylate with 10-chloromethyl-5H-dibenzo [a, d] cycloheptene. Alcohols of the Formula II, wherein R 2  represents a hydrogen atom, may be prepared from the appropriate 5H-dibenzo[a, d]cyclohepten - 10(11H) - ones via the corresponding 10 - methyl - 10, 11 - dihydro - 5H - dibenzo[a, d] cyclohepten - 10 - ols, 10 - methyl - 5H - dibenzo [a, d] cycloheptenes, and 5H - dibenzo[a, d] cycloheptene - 10 - carboxaldehydes and wherein R 2  represents a methyl group by reacting 5H- dibenzo[a, d] cycloheptene - 10 - carboxaldehyde with methylmagnesium iodide. Alcohols of the Formula II may be converted into the corresponding chlorides by treatment with thionyl chloride. 8 - Chloro - 5H - dibenzo[a, d] cyclohepten - 10(11 H) - one may be prepared from a-(pchlorophenyl - o - toluic acid via (ethyl α- (p - chlorophenyl) - o - toluate, o - (p - chlorobenzyl) benzyl alcohol, α - bromo - o - (p - chloro - benzyl) toluene, α - (p - chlorophenyl) - o - tolylacetonitrile and α - (p - chlorophenyl) - o - tolylacetic acid. 8 - Methyl - 10 - chloromethyl - 5H - dibenzo[a, d] cyclohepten - 10( 11H)- one, 8 - methoxy - 5H - dibenzo[a, d] cyclohepten- 10(11 H) - one, 8 - methylthio - 5H - dibenzo [a, d] cyclohepten - 10(11H) - one, 7, 8 - dimethyl 5H - dibenzo[a, d] cyclohepten - 10(11 H) - one and 5, 8 - dimethyl - 5H - dibenzo[a, d] cyclohepten - 10(11H) - one are prepared similarly via corresponding intermediates.