Adafenoxate

Adafenoxate

Names
Preferred IUPAC name 2-[(Adamantan-1-yl)amino]ethyl (4-chlorophenoxy)acetate
Identifiers
CAS Number	82168-26-1^N
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL2104053^N
ChemSpider	58080^Y
PubChem CID	64517
UNII	B8VQU4C05J^Y
CompTox Dashboard (EPA)	DTXSID4046280
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	363.88 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 ^YN ?) Infobox references

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.).