2-Piperidone

Chemical properties

white to yellowish low melting crystalline mass

The Uses of 2-Piperidone

δ-Valerolactam is a useful synthetic intermediate. It is an intermediate used to synthesize Cenicriviroc (C256550), an experimental drug candidate for the treatment of HIV infection. It is also a starting material for a new route to hexahydrojulolidines, using intramolecular 1,4-cycloaddition.

Definition

ChEBI: 2-Piperidone is a delta-lactam that is piperidine which is substituted by an oxo group at position 2. It has a role as an EC 1.2.1.88 (L-glutamate gamma-semialdehyde dehydrogenase) inhibitor. It is a member of piperidones and a delta-lactam.

Preparation

2-Piperidone can be obtained from cyclopentanone as raw material by a two-step reaction.

Synthesis Reference(s)

Journal of the American Chemical Society, 102, p. 7629, 1980 DOI: 10.1021/ja00546a001
Tetrahedron Letters, 28, p. 2829, 1987 DOI: 10.1016/S0040-4039(00)96220-8
The Journal of Organic Chemistry, 21, p. 965, 1956 DOI: 10.1021/jo01115a010

Purification Methods

Purify it by repeated fractional distillation.[Cowley J Org Chem 23 1330 1958, Reppe et al. Justus Liebigs Ann Chem 596 198 1955, IR: Huisgen et al. Chem Ber 90 1437 1957.] The hydrochloride has m 183-184o (from isoPrOH or EtOH/Et2O) [Hurd et al. J Org Chem 17 865 1952], and the oxime has m 122.5o (from pet ether) [Behringer & Meier Justus Liebigs Ann Chem 607 67 1957]. The picrate has m 92-93o. [Beilstein 21 H 239, 21 III/IV 3170, 21/6 V 396.]