Nipecotic acid Chemical Properties

Melting point:

261 °C (dec.) (lit.)

Boiling point:

239.22°C (rough estimate)

Density 

1.1426 (rough estimate)

refractive index 

1.4587 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

water: soluble50mg/mL, clear, colorless to faintly yellow

form 

Solid

pka

pK1:3.35(+1);pK2:10.64(0) (25°C)

color 

White

Water Solubility 

Soluble in water

Merck 

14,6560

BRN 

81096

InChI

InChI=1S/C6H11NO2/c8-6(9)5-2-1-3-7-4-5/h5,7H,1-4H2,(H,8,9)

InChIKey

XJLSEXAGTJCILF-UHFFFAOYSA-N

SMILES

N1CCCC(C(O)=O)C1

CAS DataBase Reference

498-95-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

TM6125380

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Nipecotic acid Usage And Synthesis

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

Nipecotic acid(498-95-3)Related Product Information

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• NIPECOTIC ACID ETHYL ESTER
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• Ethyl 1-benzyl-4-oxo-3-piperidinecarboxylate hydrochloride
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• 1-BENZYL-3-METHOXYCARBONYL-4-PIPERIDONE
• BENZOYLECGONINE