New tropeine derivatives

• Main Authors: ZEILE KARL, WICK HELMUT, ADICKES FRANZ
• Format: Patent
• Language: English
• Published: 08.10.1958

The invention comprises quaternary tropeines of the general formula <FORM:0802716/IV (b)/1> (wherein R is a straight-chain or branched alkyl group containing from 6-11 carbon atoms or a cyclohexyl group, R1 is an acid residue containing an aromatic group and X and Y are both hydrogen atoms or together with the adjacent carbon atoms form an oxygen bridge), and a process for their manufacture by quaternizing the corresponding tertiary tropeine with an alkyl or cyclohexyl ester of a halogen-substituted acetic acid. The reaction is carried out at room temperature, for example 20 DEG C., or, if desirable, by heating to 60 DEG C., and preferably in the presence of an inert organic solvent, for example acetonitrile, chloroform, acetone or methanol. Examples describe the preparation of diphenyl-hydroxyacetyl-N-heptoxycarbonylmethyl-tropinium bromide and chloride, N-hexoxycarbonylmethyl-scopolammonium bromide, N-octoxycarbonyl-methyl-tropinium bromide benzilic acid ester, diphenyl-hydroxyacetyl-N-octoxycarbonyl - methyl - tropinium chloride, N - cyclohexoxy - carbonylmethyl - atropinium bromide, N - nonoxycarbonylmethyl - atropinium bromide and N-heptoxycarbonylmethylscopolammonium bromide.