GB725228A - Substituted carbamic acid esters and process for the manufacture thereof - Google Patents

Abstract

The invention comprises carbamic esters of 3-quinuclidinol of the formula <FORM:0725228/IV (b)/1> where R is phenyl or cyclohexyl optionally substituted by halogen, nitro, C1-C4 alkyl or C1-C4 alkoxy and R1 represents the optional presence of one of these substituents; also their acid addition and quaternary salts. The compounds are made by treating 3-quinuclidinol with isocyanates of the formula <FORM:0725228/IV (b)/2> or (R=phenyl, R1=H) with 4 : 4-diphenyl-2 : 5-oxazolidinedione. They exist in various stereo-isomeric and optically isomeric forms. Examples show the production of the 3-quinuclidyl esters of benzhydrylcarbamic, a -cyclohexyl - benzylcarbamic, p - methylbenzhydrylcarbamic, p - chlorobenzhydrylcarbamic, p - bromobenzhydrylcarbamic, p - methoxybenzhydrylcarbamic (2 stereoisomers), pp1-dimethoxybenzhydrylcarbamic and p-nitrobenzhydrylcarbamic acids; the hydrochlorides of some are described. In addition 3-quinuclidyl benzhydrylcarbamate is converted into its quaternary salts with methyl bromide, ethyl bromide and butyl bromide, and 3-quinuclidyl a -cyclohexylbenzylcarbamate into its quaternary methobromide. Isocyanates.-The following are made from the corresponding halides and silver isocyanate: a -cyclohexylbenzyl, p-methylbenzhydryl, p - chlorobenzhydryl, p - bromobenzhydryl, p - methoxybenzhydryl, pp1-dimethoxybenzhydryl and p p-nitrobenzhydryl isocyanates. Benzhydryl halides.-p - Methylbenzhydryl chloride, p-methoxybenzhydryl chloride, pp1-dimethoxybenzhydryl chloride and p-nitrobenzhydryl chloride are made from the corresponding benzhydrols and hydrogen chloride. a -Cyclohexylbenzyl bromide is prepared by reacting benzaldehyde with cyclohexylmagnesium chloride and treating the resulting cyclohexylphenylcarbinol with phosphorus pentabromide.