Pirandamine

Synthesis

Pirandamine can be synthesized starting from 1-indanone. 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).

References

References

1. (May 1976). "Effects of tandamine and pirandamine, new potential antidepressants, on the brain uptake of norepinephrine and 5-hydroxytryptamine and related activities". Psychopharmacology.
2. (August 1976). "Pirandamine, a relatively selective 5-hydroxytryptamine uptake inhibitor". Pharmacological Research Communications.
3. (April 1977). "Effects of tandamine and pirandamine, selective blockers of biogenic amine uptake mechanisms, on gastric acid secretion and ulcer formation in the rat". Life Sciences.
4. I. Jirkovsky, L. G. Humber and R. Noureldin,Eur. J. Med. Chem., 11, 571 (1976).