Adafenoxate

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

Adafenoxate
Names
Preferred IUPAC name
2-[(Adamantan-1-yl)amino]ethyl (4-chlorophenoxy)acetate
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
InChI
  • 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 Y
    Key: PLSMXIQMWYSHIV-UHFFFAOYSA-N Y
  • 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
SMILES
  • Clc4ccc(cc4)OCC(=O)OCCNC12CC3CC(C1)CC(C2)C3
Properties
Chemical formula
 C20H26ClNO3
Molar mass 363.87834 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Synthesis
Patent:[2]

Ex 1: 4-Chlorophenoxyacetic acid (pCPA) [122-88-3] is converted to its acid chloride to give 4-chlorophenoxyacetyl chloride [4122-68-3] (1). Esterification with 2-(1-adamantylamino)ethanol [3716-66-3] (2) gives Adafenoxate (3) in a single step.

Ex 2: Same as above but Fischer–Speier esterification done via a DS-trap. This gives an 88% yield.

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.).


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