1-Methyl-4-piperidone

1-Methyl-4-piperidone
Names
Other names
1-methylpiperidin-4-one, N-Methyl-4-piperidone.
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.014.450
EC Number
  • 215-895-5
  • 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).
Infobox references

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]

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.[22] 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.[23]

A third synthesis consists of the ring closing of 1,5-dichloro-3-pentanone with methylamine.[24]

See also

References

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  2. ^ "Azacyclic compounds for use in the treatment of serotonin related diseases". Google Patents. March 6, 2001. Retrieved June 27, 2025.
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  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.
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  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. ^ US patent 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. ^ 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.
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  24. ^ "Synthesis method for N-substituted-4-piperidone". Google Patents. May 24, 2012. Retrieved June 11, 2025.
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