Oxolamine

Oxolamine

Oxolamine
Systematic (IUPAC) name
N,N-diethyl-2-(3-phenyl-1,2,4-oxadiazol-5-yl)ethanamine
Clinical data
AHFS/Drugs.com
Legal status
?
Identifiers
CAS number  Y
ATC code R05
PubChem
ChemSpider  Y
UNII  Y
KEGG  Y
ChEMBL  N
Chemical data
Formula C14H19N3O 
Mol. mass 245.32 g/mol
 N   

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