Epanolol

Epanolol is a beta blocker.^[1] developed by Imperial Chemical Industries.^[2]

Epanolol

Names
IUPAC name (RS)-N-[2-([3-(2-cyanophenoxy)-2-hydroxypropyl]amino)ethyl]-2-(4-hydroxyphenyl)acetamide
Identifiers
CAS Number	86880-51-5 Y
3D model (JSmol)	Interactive image
ChemSpider	65013 Y
KEGG	D06646 Y
PubChem CID	72014
UNII	9KGC55KP6A Y
CompTox Dashboard (EPA)	DTXSID90868959
InChI InChI=1S/C20H23N3O4/c21-12-16-3-1-2-4-19(16)27-14-18(25)13-22-9-10-23-20(26)11-15-5-7-17(24)8-6-15/h1-8,18,22,24-25H,9-11,13-14H2,(H,23,26) Y Key: YARKMNAWFIMDKV-UHFFFAOYSA-N Y
SMILES C1=CC=C(C(=C1)C#N)OCC(CNCCNC(=O)CC2=CC=C(C=C2)O)O
Properties
Chemical formula	C20H23N3O4
Molar mass	369.41432
Pharmacology
ATC code	C07AB10 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Synthesis

The ester methyl 4-benzyloxyphenylacetate (1) is treated with ethylenediamine to give the amide (3). Separately, 2-cyanophenol (4) is reacted with epichlorohydrin and sodium hydroxide to produce the benzonitrile derivative (5). Combination of (3) and (5) by heating in propanol gives (6). Lastly, catalytic hydrogenation removes the benzyl protecting group and yields epanolol.^[2][3]

See also

• Bunitrolol
• Bucindolol