Piperazine-2-carboxylic acid Chemical Properties

Melting point:

265 °C (dec.)(lit.)

Boiling point:

313.6±37.0 °C(Predicted)

Density 

1.174

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

1.90±0.20(Predicted)

Appearance

White to yellow Solid

optical activity

Consistent with structure

InChI

InChI=1S/C5H10N2O2/c8-5(9)4-3-6-1-2-7-4/h4,6-7H,1-3H2,(H,8,9)

InChIKey

JSSXHAMIXJGYCS-UHFFFAOYSA-N

SMILES

N1CCNCC1C(O)=O

CAS DataBase Reference

2762-32-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2933599590

MSDS

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

Piperazine-2-carboxylic acid Usage And Synthesis

Uses

Piperazine-2-carboxylic acid is an important organic compound used as a basic structural component of pharmaceutical intermediates. Studies have shown that Piperazine-2-carboxylic acid derivatives are a potential multi-targeted ligands (MTDLs) anti-Alzheimer's disease (AD) active ingredient.

Synthesis

Step 1: Preparation of piperazine-2-carboxylic acid: pyrazine-2-carboxylic acid (102.7 g, 0.827 mol) was dissolved in water (600 mL), sodium hydroxide (66 g, 1.65 mol) and 20% palladium/carbon catalyst (5.0 g) were added. The hydrogenation reaction was carried out under hydrogen atmosphere for 15 hours. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated. Concentrated hydrochloric acid was added to the concentrate and a white precipitate precipitated. The solid was washed with cold water, collected by filtration and dried under vacuum to give 137.2 g of piperazine-2-carboxylic acid hydrochloride (99.6% yield). Mass spectrum (MS): m/z 131 (corresponding to C5H10N2O2, [M+H]+).

References

[1] Tetrahedron Letters, 1989, vol. 30, # 39, p. 5193 - 5196
[2] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 8, p. 1121 - 1126
[3] Patent: US6251919, 2001, B1

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