Verfahren zur Herstellung von basisch substituierten Cycloalkenderivaten

The invention comprises compounds of the formula wherein R1 represents an alkyl radical containing 1-4 carbon atoms and n represents the numbers 0, 1 or 2, and salts of these compounds; and a process for their preparation (a) by reacting a compound of the formula wherein R2 represents an alkyl radical with 1 to 3 carbon atoms, an aryl or an aralkyl radical, with mixtures of hydrobromic acid and organic or inorganic acids, preferably glacial acetic acid, or (b) by reacting a compound of the formula with dehydrating agents, preferably at elevated temperature, and isomerizing the resulting compound by means of aqueous or gaseous hydrogen bromide or mixtures of hydrobromic acid with suitable acids or solvents. The hydrobromic acid salts so obtained can be converted to salts of other acids, preferably by treatment with an appropriate silver salt. The ethers of 1-m-hydroxyphenyl-2-(methylalkyl - aminomethyl) cycloalkanols (II) are made by forming a Grignard reagent from the appropriate ether of m-bromophenol and reacting with a 2-(methyl-alkyl-aminomethyl)-cycloalkanone. The ether can be hydrogenated in the presence of palladium on charcoal to form the corresponding 1-m-hydroxyphenyl-(2 - methyl - alkyl - aminomethyl) - cycloalkanol-(1) (III).