Pirandamine
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.

Synthesis

The Reformatsky reaction between 1-indanone [83-33-0] (1) and ethyl bromoacetate [105-36-2] in the presence of zinc gives ethyl 2-(1-hydroxy-2,3-dihydroinden-1-yl)acetate [1620-02-6] (2). The reduction of the ester with ester with LiAlH4 gives  1-(2-hydroxyethyl)-2,3-dihydroinden-1-ol, CID:130147665 (3). Acid catalyzed dehydration then leads to indene-3-ethanol [57931-97-2] (4'). Acid catalyzed condensation with ethyl acetoacetate [141-97-9] then gives CID:53692067 (5) The saponification of the ester to the corresponding acid [52001-26-0]. The reaction of this with ethyl chloroformate would give a mixed anhydride, and further reaction of this with dimethylamine then led to the amide [52001-28-2] (6). Reduction with lithium aluminium hydride completes the synthesis of pirandamine (7).

See also 
 Tandamine
Prindamine (21489-22-5)

References 

Dihydropyrans