4-Phenylpiperidine

4-Phenylpiperidine is a chemical compound. It features a benzene ring bound to a piperidine ring.

4-Phenylpiperidine
Names
IUPAC name
4-Phenylpiperidine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.011.130
UNII
Properties
C11H15N
Molar mass 161.248 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

4-Phenylpiperidine is the base structure for a variety of opioids, such as pethidine (meperidine), ketobemidone, alvimopan, loperamide, and diphenoxylate.

Preparation
  1. From the 3° alcohol, dehydration of which, and subsequent catalytic hydrogenation furnishes the product.
  2. 4-Phenylpyridine can also be catalytically hydrogenated.

Derivatives

Drugs derived from 4-phenylpiperidine proper include:

  1. 4-PPBP
  2. ADX-71149
  3. Ropitoin
  4. Altapizone
  5. Vesamicol
  6. JNJ-42153605
  7. #81 & #82, #160 & #162, #165, #166 & #167, #174 & #178 in U.S. Patent 6,057,371
  8. Bromination of 4-PP gives para-bromo-4-PP [80980-89-8] U.S. Patent 6,303,593. See also:[1]
  9. Guzikowski & Tamiz had some interesting example too:[2]
  10. JNJ-40068782
  11. PC21481466 i.e. 5,5-Diphenyl-3-[2-(4-phenyl-piperidin-1-yl)-ethyl]-imidazolidine-2,4-dione.

4-phenylpiperdine core include:

  1. Haloperidol
  2. Enefexine
  3. Huntexil

A related compound is 4-benzylpiperidine, in which the rings are separated by a methylene bridge.

See also

References
  1. Wenzel, Barbara; Sorger, Dietlind; Heinitz, Katrin; Scheunemann, Matthias; Schliebs, Reinhard; Steinbach, Joerg; Sabri, Osama European Journal of Medicinal Chemistry, 2005 , vol. 40, # 12 p. 1197 - 1205
  2. Guzikowski, Anthony P.; Tamiz, Amir P.; Acosta-Burruel, Manuel; Hong-Bae, Soo; Cai, Sui Xiong; Hawkinson, Jon E.; Keana, John F. W.; Kesten, Suzanne R.; Shipp, Christina T.; Tran, Minhtam; Whittemore, Edward R.; Woodward, Richard M.; Wright, Jon L.; Zhou, Zhang-Lin (2000). "Synthesis ofN-Substituted 4-(4-Hydroxyphenyl)piperidines, 4-(4-Hydroxybenzyl)piperidines, and (±)-3-(4-Hydroxyphenyl)pyrrolidines: Selective Antagonists at the 1a/2B NMDA Receptor Subtype". Journal of Medicinal Chemistry. 43 (5): 984–994. doi:10.1021/jm990428c. ISSN 0022-2623.
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