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4-Phenylpiperidine

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4-Phenylpiperidine
Names
IUPAC name
4-Phenylpiperidine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.011.130 Edit this at Wikidata
  • InChI=1S/C11H15N/c1-2-4-10(5-3-1)11-6-8-12-9-7-11/h1-5,11-12H,6-9H2 checkY
    Key: UTBULQCHEUWJNV-UHFFFAOYSA-N checkY
  • InChI=1/C11H15N/c1-2-4-10(5-3-1)11-6-8-12-9-7-11/h1-5,11-12H,6-9H2
    Key: UTBULQCHEUWJNV-UHFFFAOYAO
  • c1cc(ccc1)C2CCNCC2
  • c1ccc(cc1)C2CCNCC2
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).
☒N verify (what is checkY☒N ?)

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

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]

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