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Antitussive
Fedrilate
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Fedrilate

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Fedrilate
Fedrilate.png
Clinical data
Trade names Tussefan
ATC code
Identifiers
  • 4-morpholin-4-ylbutan-2-yl 4-phenyloxane-4-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
ECHA InfoCard 100.041.390
Chemical and physical data
Formula C20H29NO4
Molar mass 347.455 g·mol−1
3D model (JSmol)
  • O=C(OC(CCN1CCOCC1)C)C3(c2ccccc2)CCOCC3
  • InChI=1S/C20H29NO4/c1-17(7-10-21-11-15-24-16-12-21)25-19(22)20(8-13-23-14-9-20)18-5-3-2-4-6-18/h2-6,17H,7-16H2,1H3 checkY
  • Key:RDEOYUSTRWNWLX-UHFFFAOYSA-N checkY
  (verify)

Fedrilate is a centrally acting cough suppressant. It was patented as a mucolytic by UCB in 1971, but was never brought to market in the US. In the Netherlands, it has been marketed as Tussefan and in combination with guaifenesin as Tussefan expectorans.

Synthesis

Patents: Starting acid:

Sodamide alkylation between benzyl cyanide (1) and bis(chloroethyl)ether [111-44-4] (2) gives 4-phenyloxane-4-carbonitrile [1202-81-9] (3). Hydrolysis of the nitrile gives 4-phenyloxane-4-carboxylic acid [182491-21-0] (4). Treatment with thionyl chloride gives the corresponding acid chloride (5). Ester formation with 4-(morpholin-4-yl)butan-2-ol [858440-45-6] (6) gives Fedrilate proper (7).




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