Chemical Properties
off-white to pale yellow-beige powder
Uses
(+/-)-Nipecotic Acid (cas# 498-95-3) is a compound useful in organic synthesis.
Definition
ChEBI: A piperidinemonocarboxylic acid that is piperidine in which one of the hydrogens at position 3 is substituted by a carboxylic acid group.
Synthesis Reference(s)
The Journal of Organic Chemistry, 28, p. 602, 1963
DOI: 10.1021/jo01037a531
General Description
R()-Nipecotic acid is a potential inhibitor of uptake of γ-aminobutyric acid (GABA) in rat brain slices. Lipophilic derivatives of nipecotic acid are used as drugs for the treatment of epilepsy.
Synthesis
The general procedure for the synthesis of 3-piperidinecarboxylic acid from methyl nicotinate was as follows: 0.25 g of methyl nicotinate with HRO/Na-β catalyst (50 mg) in 40 mL of deionized water was added to the reactor. Subsequently, the reactor was subjected to hydrogen pressure of 15 bar and heated at 120 °C for 1 h of reaction. Upon completion of the reaction, the catalyst was separated by centrifugation and the resulting mixture of clarified products was analyzed using GC-MS. The reaction achieved 100% conversion of methyl nicotinate and gave 3-piperidinecarboxylic acid in 100% yield.
References
[1] Patent: WO2017/60922, 2017, A1. Location in patent: Page/Page column 15; 22
