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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.

References