1-Methyl-4-piperidone

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]

1-Methyl-4-piperidone

Names
Other names 1-methylpiperidin-4-one, N-Methyl-4-piperidone.
Identifiers
CAS Number	1445-73-4 Y
3D model (JSmol)	Interactive image
ChemSpider	66668
ECHA InfoCard	100.014.450
EC Number	215-895-5
PubChem CID	74049
CompTox Dashboard (EPA)	DTXSID20162735
InChI InChI=1S/C6H11NO/c1-7-4-2-6(8)3-5-7/h2-5H2,1H3 Key: HUUPVABNAQUEJW-UHFFFAOYSA-N
SMILES CN1CCC(=O)CC1
Properties
Chemical formula	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

Applications

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

• AC-90179^[2]
• B777-81^[3][4][5]
• Bamipine^[6]
• DDD-016^[7]
• Hepzidine^[8]
• LY-334370^[9]
• Mebhydrolin^[10][11]
• Naratriptan^[12][13]
• MPPP^[14]
• Picenadol^[15]
• Pimavanserin^[16]
• Pimethixene^[17]
• Piperylone^[18][19][20]
• SN-22^[21]

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

• 4-Piperidone, the parent compound