Adafenoxate is a compound related to centrophenoxine, that has been found to act as a nootropic in rats.[1]

Synthesis

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

Adafenoxate synthesis

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

References

  1. ^ Petkov VD, Getova D, Mosharrof AH (1987). "A study of nootropic drugs for anti-anxiety action". Acta Physiol Pharmacol Bulg. 13 (4): 25–30. PMID 2896427.
  2. ^ Romeo R. Andreoli, Xavier D. Cirera, U.S. patent 4,476,319 (1984 to Sociedad Espanola De Especialidades Farmaco-Terapeuticas S.A.).