Pirandamine

Pirandamine is a tricyclic derivative which acts as a selective serotonin [reuptake inhibitor]. It was investigated in the 1970s as a potential antidepressant but clinical development was not commenced and it was never marketed. Pirandamine is structurally related to tandamine, which, in contrast, is a selective norepinephrine reuptake inhibitor.

Synthesis

Pirandamine can be synthesized starting from 1-indanone. The Reformatsky reaction between 1-indanone and ethyl bromoacetate in the presence of zinc gives ethyl 2-acetate. The reduction of the ester with ester with lithium [aluminum hydride] gives 1--2,3-dihydroinden-1-ol. Acid-catalyzed dehydration then leads to indene-3-ethanol. Acid-catalyzed condensation with ethyl acetoacetate then gives. The saponification of the ester then gives the corresponding acid. The reaction of this with ethyl chloroformate gives a mixed anhydride, and further reaction of this with dimethylamine then leads to the amide . Reduction with lithium aluminium hydride completes the synthesis of pirandamine.