Diphepanol
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Names | |
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IUPAC name 1,1-diphenyl-2-(piperidin-1-yl)propan-1-ol | |
Identifiers | |
3D model (JSmol) |
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ChemSpider | |
ECHA InfoCard | 100.007.372 |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C20H25NO | |
Molar mass | 295.42 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Diphepanol is a cough suppressant (antitussive).
Synthesis
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Ex 1: The α-keto bromination of propiophenone [93-55-0] (1) gives 2-bromopropiophenone [2114-00-3] (2). Displacement of the halogen and hence amination with piperidine [110-89-4] gave alpha-Piperidinopropiophenone, CID:458526 (3). and addition of phenyl Grignard reagent to give the benzhydrol product, and hence Dihepanol (4).
See also
References
- ^ Moehre, H.; Kamper, Ch. Pharmazie, 1983 , vol. 38, # 8 p. 512 – 520.
- ^ L. Stein and E. Lindner, U.S. patent 2,827,460 (1958 to Hoechst)