Epanolol
Chemical compound
From Wikipedia, the free encyclopedia
Epanolol is a beta blocker.[1] developed by Imperial Chemical Industries.[2]
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| Names | |
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| IUPAC name
(RS)-N-[2-([3-(2-cyanophenoxy)-2-hydroxypropyl]amino)ethyl]-2-(4-hydroxyphenyl)acetamide | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C20H23N3O4 | |
| Molar mass | 369.41432 |
| Pharmacology | |
| C07AB10 (WHO) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]
