1-Methyl-4-piperidone

Last updated
1-Methyl-4-piperidone
1-methyl-4-piperidone.svg
Names
Preferred IUPAC name
1-Methylpiperidin-4-one
Other names
N-Methyl-4-piperidone.
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.014.450 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 215-895-5
PubChem CID
  • InChI=1S/C6H11NO/c1-7-4-2-6(8)3-5-7/h2-5H2,1H3
    Key: HUUPVABNAQUEJW-UHFFFAOYSA-N
  • CN1CCC(=O)CC1
Properties
C6H11NO
Molar mass 113.16 g/mol
Density 0.92–0.98 g/cm3 (20°C)
Boiling point 55–60 °C (131–140 °F; 328–333 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1-Methyl-4-piperidone (also known as N-methyl-4-piperidone) is a clear dark yellow liquid organic compound with molecular formula C7H11NO. It is the N-methyl substituted variant of 4-piperidone. [1]

Contents

Applications

It is used as a building block for a variety of pharmaceuticals including:

Synthesis

The first synthesis of 1-methyl-4-piperidone was reported by Samuel M. McElvain in 1948. [23] The method involves double Michael reaction between methylamine and two equivalents of ethyl acrylate, a Dieckmann cyclization (i.e. intramolecular Claisen condensation), saponification and decarboxylation.

Another synthesis uses methylamine, formaldehyde and the ethyl ester of acetonedicarboxylic acid. [24]

A third synthesis consists of the ring closing of 1,5-dichloro-3-pentanone with methylamine. [25]

See also

References

  1. ↑ "SAFETY DATA SHEET" . Retrieved 2025-06-11.
  2. ↑ "Azacyclic compounds for use in the treatment of serotonin related diseases". Google Patents. March 6, 2001. Retrieved June 27, 2025.
  3. ↑ Eistetter K, Kley HP, Menge HG, Schaefer H (1983). "B-777-81". Drugs of the Future. 8 (5): 387. doi:10.1358/dof.1983.008.05.65796.
  4. ↑ "Anti-depressant and analgesic 4-phenoxypiperidines". Google Patents. July 11, 1980. Retrieved June 11, 2025.
  5. ↑ "4-Aryl-4-aryloxypiperidines". Google Patents. September 3, 1980. Retrieved June 11, 2025.
  6. ↑ "X-tertiary amino-i-alkyl-piperidines". Google Patents. July 13, 1954. Retrieved June 11, 2025.
  7. ↑ Bandyopadhyaya, Achintya; Rajagopalan, Desikan R.; Rath, Nigam P.; Herrold, Amy; Rajagopalan, Raghavan; Napier, T. Celesete; Tedford, Clark E.; Rajagopalan, Parthasarathi (2012). "The synthesis and receptor binding affinities of DDD-016, a novel, potential, atypical antipsychotic" . MedChemComm. 3 (5): 580. doi:10.1039/c2md00311b. ISSN   2040-2503 . Retrieved 2025-06-11.
  8. ↑ van Der Stelt, C.; Harms, A. F.; Nauta, W. Th. (1961). "The Effect of Alkyl-Substitution in Drugs--V. Synthesis and Chemical Properties of Some Dibenzo [a,d]1,4-cycloheptadienyl Ethers" . Journal of Medicinal and Pharmaceutical Chemistry. 4 (2): 335–349. doi:10.1021/jm50018a008. ISSN   0095-9065. PMID   14039500 . Retrieved 2025-06-26.
  9. ↑ Filla, Sandra A.; Mathes, Brian M.; Johnson, Kirk W.; Phebus, Lee A.; Cohen, Marlene L.; Nelson, David L.; Zgombick, John M.; Erickson, Jon A.; Schenck, Kathryn W.; Wainscott, David B.; Branchek, Theresa A.; Schaus, John M. (2003-07-01). "Novel Potent 5-HT 1F Receptor Agonists: Structure−Activity Studies of a Series of Substituted N -[3-(1-Methyl-4-piperidinyl)-1 H -pyrrolo[3,2- b ]pyridin-5-yl]amides" . Journal of Medicinal Chemistry. 46 (14): 3060–3071. doi:10.1021/jm030020m. ISSN   0022-2623. PMID   12825944 . Retrieved 2025-06-11.
  10. ↑ Hörlein, Ulrich (1954). "Zur Kenntnis der Tetrahydrocarbolin-Verbindungen (I. Mitteil.)" . Chemische Berichte. 87 (4): 463–472. doi:10.1002/cber.19540870404. ISSN   0009-2940 . Retrieved 2025-06-11.
  11. ↑ "Preparation method of mebhydrolin napadisylate". Google Patents. 2013-01-31. Retrieved 2025-06-11.
  12. ↑ "Process for preparation of naratriptan hydrochloride". Google Patents. 2009-03-09. Retrieved 2025-06-11.
  13. ↑ "A process for the synthesis of naratriptan". Google Patents. 2010-08-18. Retrieved 2025-06-11.
  14. ↑ "Molecule of the Month August 2023". School of Chemistry. 2016-08-18. Retrieved 2025-06-11.
  15. ↑ "Process for preparation of substituted formamidine and substituted N-iminomethyl piperidine". Google Patents. 1983-03-17. Retrieved 2025-06-11.
  16. ↑ "Deuterated pimavanserin 1- (4-flu0r0benzyl) -3- (4-isobutoxybenzyl) -1- ( l-methyl-piperidin-4-yl) -urea". Google Patents. May 8, 2008. Retrieved June 27, 2025.
  17. ↑ "Insecticidal tricyclic derivatives". Google Patents. 2003-09-12. Retrieved 2025-06-11.
  18. ↑ USpatent 2903460,Jucker E, Ebnother A, Lindenmann AJ,"Pyrazolone derivatives",issued 1959-09-08, assigned to Sandoz AG
  19. ↑ Ebnöther A, Jucker E, Lindenmann A (1959). "Über neuartige, basisch substituierte Pyrazolon-Derivate. Untersuchungen über synthetische Arzneimittel. 3. Mitteilung". Helvetica Chimica Acta. 42 (4): 1201–1214. doi:10.1002/hlca.19590420415.
  20. ↑ "Piperylone". Pharmaceutical Substances. Thieme. Retrieved 2024-07-17.
  21. ↑ Cole, Derek C.; Ellingboe, John W.; Lennox, William J.; Mazandarani, Hossein; Smith, Deborah L.; Stock, Joseph R.; Zhang, Guoming; Zhou, Ping; Schechter, Lee E. (2005). "N1-arylsulfonyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole derivatives are potent and selective 5-HT6 receptor antagonists". Bioorganic & Medicinal Chemistry Letters. 15 (2). Elsevier BV: 379–383. doi:10.1016/j.bmcl.2004.10.064. ISSN   0960-894X. PMID   15603958.
  22. ↑ Butler, K. V., Kalin, J., Brochier, C., Vistoli, G., Langley, B., Kozikowski, A. P. (11 August 2010). "Rational Design and Simple Chemistry Yield a Superior, Neuroprotective HDAC6 Inhibitor, Tubastatin A". Journal of the American Chemical Society. 132 (31): 10842–10846. doi:10.1021/ja102758v.
  23. ↑ McElvain, S. M., Rorig, K. (May 1948). "Piperidine Derivatives. XVIII. The Condensation of Aromatic Aldehydes with 1-Methyl-4-piperidone". Journal of the American Chemical Society. 70 (5): 1820–1825. Bibcode:1948JAChS..70.1820M. doi:10.1021/ja01185a051. PMID   18861789.
  24. ↑ "A kind of synthetic method of N- methyl -4- piperidones". Google Patents. September 3, 2019. Retrieved June 11, 2025.
  25. ↑ "Synthesis method for N-substituted-4-piperidone". Google Patents. May 24, 2012. Retrieved June 11, 2025.
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