Adafenoxate

Adafenoxate is a compound related to centrophenoxine, that has been found to act as a nootropic in rats.

Synthesis
Adafenoxate can be prepared starting with 4-chlorophenoxyacetic acid (pCPA) by converting it to its acid chloride to give 4-chlorophenoxyacetyl chloride (1). Esterification with 2-(1-adamantylamino)ethanol (2) gives adafenoxate (3).



Alternatives, the final step can be accomplished via Fischer–Speier esterification using a Dean-Stark trap.