Ringerweiterungen bei Reaktionen von 2‐[N‐Methyl‐pyrrolidinyl‐(2)]‐1‐chlor‐äthan und 2‐[N‐Methyl‐poperidyl‐(2)]‐1‐chlor‐äthan mit nucleophilen Reagenzien. Untersuchungen über synthetische Arzneimittel, 13. Mitteilung

With nucleophilic reagents the γ‐aminoalkyl halides 2‐[N‐methyl‐pyrrolidinyl‐(2)]‐ and 2‐[N‐methyl‐piperidyl‐(2)]‐1‐chloro‐ethane (I and XVII) give, in addition to the normal reaction products, isomers having a ring expanded by two C‐atoms. As intermediates quaternary azetidinium ions are formed which are attacked by the nucleophilic reagent with opening of a C‐N bond of the azetidine ring. In this way, pyrrolidine and hexahydroazepine derivatives are formed from I with about equal probability, whereas XVII preferentially gives six‐membered ring compounds.