DL-Nipecotic acid

Chemical properties

off-white to pale yellow-beige powder

The Uses of DL-Nipecotic acid

(+/-)-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

Firstly 3-piperidine formamides or their salts were reacted with concentrated hydrochloric acid which produces the (S)-3-piperidine carboxylic acid salt. Then the salt of (S)-3-piperidine carboxylic acid was converted to 3-piperidine carboxylic acid (final product) via stirring with potassium hydroxide in methanol. The synthesized final product was characterized using the 1HNMR technique with data as 1H NMR (401 MHz, D2O) δ 3.34 (dd, J = 12.6, 3.6 Hz, 1H), 3.29-3.19 (m, 1H), 3.15-2.98 (m, 2H), 2.66-2.55 (m, 1H), 2.06–1.96 (m, 1H), 1.95–1.82 (m, 1H), 1.82-1.63 (m, 2H).