Oxolamine

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Oxolamine
Oxolamine.png
Systematic (IUPAC) name
N,N-diethyl-2-(3-phenyl-1,2,4-oxadiazol-5-yl)ethanamine
Clinical data
AHFS/Drugs.com International Drug Names
Legal status ?
Identifiers
CAS number 959-14-8 YesY
ATC code R05DB07
PubChem CID 13738
ChemSpider 13143 YesY
UNII 90BEA145GY YesY
KEGG D07387 YesY
ChEMBL CHEMBL1620875 N
Chemical data
Formula C14H19N3O 
Mol. mass 245.32 g/mol
 N (what is this?)  (verify)

Oxolamine is a cough suppressant.

Synthesis[edit]

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.

Oxolamine rxn scheme.png

DE 1097998