Aminoalkylation of metal derivatives of indole. Part II. Coupling of indolylmagnesium iodides with halogenoalkylamines

Abstract

The coupling between indole Grignard reagents and halogenoalkylamines provides a general synthesis of 3-aminoalkylindoles. The reaction of indolylmagnesium iodide with 2-chloro-1-dimethylaminopropane furnishes a mixture of four isomeric amines which have been identified by alternative syntheses. The results indicate that although an aziridinium ion participates in this reaction it is not the main electrophilic agent.