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Oxolamine

Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	R05DB07 (WHO)
Identifiers
IUPAC name N,N-diethyl-2-(3-phenyl-1,2,4-oxadiazol-5-yl)ethanamine
CAS Number	959-14-8
PubChem CID	13738
ChemSpider	13143
UNII	90BEA145GY
KEGG	D07387
CompTox Dashboard (EPA)	DTXSID5023403
ECHA InfoCard	100.012.267
Chemical and physical data
Formula	C14H19N3O
Molar mass	245.32 g/mol g·mol
3D model (JSmol)	Interactive image
SMILES n1c(onc1c2ccccc2)CCN(CC)CC
InChI InChI=1S/C14H19N3O/c1-3-17(4-2)11-10-13-15-14(16-18-13)12-8-6-5-7-9-12/h5-9H,3-4,10-11H2,1-2H3 Key:IDCHQQSVJAAUQQ-UHFFFAOYSA-N
(verify)

Oxolamine is a cough suppressant.

Synthesis

The syntheses of 1,2,4-oxadiazole systems all rely on hydroxylamine for providing a preformed N-O linkage. The preparation of the respiratory anti-inflammatory and antitussive agent oxolamine starts by acylation of the alkoxide from the N-hydroxyamidine with 3-chloropropionyl chloride; the presence of the negative charge on oxygen results in the formation of the O-acylated product. Treatment of that intermediate with triethylamine leads to cyclization via imine formation to afford the 1,2,4-oxadiazole. Displacement of the terminal chlorine with diethylamine gives the corresponding amine oxolamine.

DE 1097998 

• Antitussives
• Oxadiazoles
• Amines