Adafenoxate

Source: Wikipedia, the free encyclopedia.
Adafenoxate
Names
Preferred IUPAC name
2-[(Adamantan-1-yl)amino]ethyl (4-chlorophenoxy)acetate
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C20H26ClNO3/c21-17-1-3-18(4-2-17)25-13-19(23)24-6-5-22-20-10-14-7-15(11-20)9-16(8-14)12-20/h1-4,14-16,22H,5-13H2 checkY
    Key: PLSMXIQMWYSHIV-UHFFFAOYSA-N checkY
  • InChI=1/C20H26ClNO3/c21-17-1-3-18(4-2-17)25-13-19(23)24-6-5-22-20-10-14-7-15(11-20)9-16(8-14)12-20/h1-4,14-16,22H,5-13H2
    Key: PLSMXIQMWYSHIV-UHFFFAOYAK
  • Clc4ccc(cc4)OCC(=O)OCCNC12CC3CC(C1)CC(C2)C3
Properties
C20H26ClNO3
Molar mass 363.88 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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).

Esterification
with 2-(1-adamantylamino)ethanol (2) gives adafenoxate (3).

Adafenoxate synthesis

Alternatives, the final step can be accomplished via

Dean-Stark trap
.

References

  1. 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.).