Pirandamine

 ( Dihydropyrans ) 

Pirandamine ( AY-23,713) is a tricyclic derivative which acts as a selective serotonin reuptake inhibitor (SSRI). 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.

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Synthesis Pirandamine can be synthesized starting from 1-indanone.I. Jirkovsky, L. G. Humber and R. Noureldin,Eur. J. Med. Chem., 11, 571 (1976). The Reformatsky reaction between 1-indanone ( 1) and ethyl bromoacetate in the presence of zinc gives ethyl 2-(1-hydroxy-2,3-dihydroinden-1-yl)acetate ( 2). The reduction of the ester with ester with lithium aluminum hydride (LiAlH₄) gives 1-(2-hydroxyethyl)-2,3-dihydroinden-1-ol ( 3). Acid-catalyzed dehydration then leads to indene-3-ethanol ( 4). Acid-catalyzed condensation with ethyl acetoacetate then gives ( 5). 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 ( 6). Reduction with lithium aluminium hydride completes the synthesis of pirandamine ( 7).

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See also

• Tandamine

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