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Diphepanol

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Diphepanol
Names
IUPAC name 1,1-diphenyl-2-(piperidin-1-yl)propan-1-ol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.372 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C20H25NO/c1-17(21-15-9-4-10-16-21)20(22,18-11-5-2-6-12-18)19-13-7-3-8-14-19/h2-3,5-8,11-14,17,22H,4,9-10,15-16H2,1H3
SMILES
  • OC(c1ccccc1)(c2ccccc2)C(N3CCCCC3)C
Properties
Chemical formula C20H25NO
Molar mass 295.42
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Diphepanol is a cough suppressant (antitussive).

Synthesis

Synthesis: Patent:

Ex 1: The α-keto bromination of propiophenone (1) gives 2-bromopropiophenone (2). Displacement of the halogen and hence amination with piperidine gave alpha-Piperidinopropiophenone, CID:458526 (3). and addition of phenyl Grignard reagent to give the benzhydrol product, and hence Dihepanol (4).

See also

References

  1. Moehre, H.; Kamper, Ch. Pharmazie, 1983 , vol. 38, # 8 p. 512 – 520.
  2. L. Stein and E. Lindner, U.S. patent 2,827,460 (1958 to Hoechst)
Cough and cold preparations (R05)
Expectorants
Mucolytics
Cough suppressants
Opium alkaloids,
opioids,
and derivatives
Other


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