1-Methyl-4-piperidone
1-Methyl-4-piperidone is a clear dark yellow liquid organic compound with molecular formula. It is the N-methyl substituted variant of 4-piperidone.
Applications
It is used as a building block for a variety of pharmaceuticals including:- AC-90179
- B777-81
- Bamipine
- DDD-016
- Diphenylpyraline
- Hepzidine
- Latrepirdine & AVN-101 & Dorastine.
- Lortalamine
- LY-334370
- Mebhydrolin
- Naratriptan
- MPPP
- Picenadol
- Pimavanserin
- Pimethixene
- Piperylone
- SN-22
- Tubastatin A TFA salt:
Synthesis
The first synthesis of 1-methyl-4-piperidone was reported by Samuel M. McElvain in 1948. The method involves double Michael reaction between methylamine and two equivalents of ethyl acrylate, a Dieckmann cyclization, saponification and decarboxylation.Another synthesis uses methylamine, formaldehyde and the ethyl ester of acetonedicarboxylic acid.
A third synthesis consists of the ring closing of 1,5-dichloro-3-pentanone with methylamine.