A number of indole and benzofuran derivatives carrying a dialkylaminomcthyl side chain at the 2-position have been prepared as serotonin analogues.It is hoped that these compounds might have serotonin-like or anti-serotonin activities.2-Indole carboxylic acid, 5-methoxyindole-2-carboxylic acid and coumarilic acid were converted into the corresponding acyl chlorides, which, on condensation with various secondary amines such as diethyl amine, di-n-butyl amine, pyrrolidine, piperidine and morpholine, gave the corresponding amides.Attempts to prepare 5-methoxycoumarilyl chloride by a similar process were not successful.The acid was then converted into the corresponding acyl azide, which gave the N, N-disubstituted 5-methoxycoumarilamides on interaction with the secondary amines.Reduction of these amides by means of lithium aluminium hydride gave the expected amines(Ⅲ-Ⅵ).