1-Methyl-4-piperidone
Chemical compound
From Wikipedia, the free encyclopedia
1-Methyl-4-piperidone (also known as N-methyl-4-piperidone) is a clear dark yellow liquid organic compound with molecular formula C6H11NO. It is the N-methyl substituted variant of 4-piperidone.[1]
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| Names | |
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| Preferred IUPAC name
1-Methylpiperidin-4-one | |
| Other names
N-Methyl-4-piperidone. | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.014.450 |
| EC Number |
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PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C6H11NO | |
| Molar mass | 113.16 g/mol |
| Density | 0.92â0.98 g/cm3 (20°C) |
| Boiling point | 55â60 °C (131â140 °F; 328â333 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]
- Diphenylpyraline
- Hepzidine[8]
- Latrepirdine & AVN-101 (aka Maritupirdine) & Dorastine.
- Lortalamine
- LY-334370[9]
- Mebhydrolin[10][11]
- Naratriptan[12][13]
- MPPP[14]
- Picenadol[15]
- Pimavanserin[16]
- Pimethixene[17]
- Piperylone[18][19][20]
- RS-86 [3576-73-6] Fumarate salt: [51382-46-8][21][22]
- SN-22[23]
- Tienocarbine[24]
- Tubastatin A [1252003-15-8] TFA salt: [1239262-52-2][25]
Synthesis
The first synthesis of 1-methyl-4-piperidone was reported by Samuel M. McElvain in 1948.[26] 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.[27]
A third synthesis consists of the ring closing of 1,5-dichloro-3-pentanone with methylamine.[28]
See also
- 4-Piperidone, the parent compound
