Efaroxan

Efaroxan

Clinical data
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name 2-(2-ethyl-2,3-dihydro-1-benzofuran-2-yl)-4,5-dihydro-1H-imidazole
CAS Number	89197-32-0 Y
PubChem CID	72016
ChemSpider	65015 Y
UNII	G00490L21H
ChEMBL	ChEMBL57895 Y
CompTox Dashboard (EPA)	DTXSID8045149
Chemical and physical data
Formula	C13H16N2O
Molar mass	216.284 g·mol−1
3D model (JSmol)	Interactive image
SMILES N\1=C(\NCC/1)C3(Oc2ccccc2C3)CC
InChI InChI=1S/C13H16N2O/c1-2-13(12-14-7-8-15-12)9-10-5-3-4-6-11(10)16-13/h3-6H,2,7-9H2,1H3,(H,14,15) Y Key:RATZLMXRALDSJW-UHFFFAOYSA-N Y
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Efaroxan is an α₂-adrenergic receptor antagonist and antagonist of the imidazoline receptor.

Synthesis

Synthesis (Cmp#13): Revised:

The Darzens reaction between 2-fluorobenzaldehyde [57848-46-1] (1) and Ethyl 2-bromobutyrate [533-68-6] (2) gives ethyl 2-ethyl-3-(2-fluorophenyl)oxirane-2-carboxylate, CID:100942311 (3). A catalytic hydrogenation over Pd/C would give ethyl 2-[(2-fluorophenyl)methyl]-2-hydroxybutanoate, CID:77591056 (4). Saponification of the ester then gives 2-[(2-Fluorophenyl)methyl]-2-hydroxybutanoic acid, CID:53869347 (5). Treatment with 2 molar equivalents of sodium hydride apparently gives 2-Ethyl-2,3-dihydrobenzofuran-2-carboxylic acid [111080-50-3] (6). Treatment of the carboxylic acid with thionyl chloride then gives the acid chloride and subsequent treatment of this with ethylenediamine in the presence of trimethylaluminium completed the synthesis of Efaroxan (8).

See also

• Fluparoxan
• Idazoxan

External links

• Media related to Efaroxan at Wikimedia Commons