Chemistry: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
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

Tracking categories (test):

• SizeSet

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

Synthesis

Patent:

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.