2-Piperazinone Chemical Properties

Melting point:

136-140 °C (lit.)

Boiling point:

164°C/5mmHg(lit.)

Density 

1.053±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform

form 

Crystalline Powder

pka

15.47±0.20(Predicted)

color 

White to tan

Sensitive 

Hygroscopic

Stability:

Stable, but may be light and moisture sensitive. Incompatible with oxidizing agents.

InChI

InChI=1S/C4H8N2O/c7-4-3-5-1-2-6-4/h5H,1-3H2,(H,6,7)

InChIKey

IWELDVXSEVIIGI-UHFFFAOYSA-N

SMILES

N1CCNCC1=O

CAS DataBase Reference

5625-67-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-43

Safety Statements 

26-36/37

RIDADR 

1759

WGK Germany 

3

HazardClass 

8

PackingGroup 

III

HS Code 

29349990

MSDS

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

2-Piperazinone Usage And Synthesis

Chemical Properties

solid

Uses

2-Piperazinone (cas# 5625-67-2) is a compound useful in organic synthesis.

Definition

ChEBI: Piperazine-2-one is a carboximidic acid.

Synthesis

The general procedure for the synthesis of 2-piperazinone from ethyl chloroacetate and ethylenediamine was as follows: ethyl chloroacetate (4.9 g, 40 mmol) was dissolved in 40 mL of anhydrous ethanol and slowly added dropwise to 100 mL of ethylenediamine (24 g, 400 mmol) over 3.5 hours at room temperature. After the dropwise addition, the reaction mixture was allowed to stand for 2 hours. Subsequently, sodium ethoxide (15 mL, 40 mmol, 21% w/w denatured ethanol solution) was added, the precipitated sodium chloride was removed by filtration and the solvent was evaporated. To the resulting red oil 40 mL of DMF was added and stirred at room temperature for 24 h. The mixture was then heated at 60°C to 70°C while N2 gas was passed through to remove volatiles. The resulting yellow solid was separated by silica gel column chromatography, eluting using a solvent mixture (CHCl3:MeOH:NH4OH = 9:1:0.1) to give the crude product (3.3 g, 33 mmol, 82% yield). This yellow solid was used directly in the next step of the reaction without further purification. Pure white crystals were obtained by three times recrystallization from acetone.1H NMR (CDCl3): δ 1.70 (1H, br s), 3.03 (2H, t, J = 5.4 Hz), 3.37 (2H, td, J = 2.3, 5.4 Hz), 3.52 (2H, s), 6.54 (1H, br s).13C NMR (CDCl3): δ 42.31, 43.05, 49.83, 170.00. melting point: 132°C-134°C (uncorrected) [literature value: 136°C (corrected)] (American Chemical Society Journal, 62 (1940) 1202-1204).

References

[1] Patent: US2005/222166, 2005, A1. Location in patent: Page/Page column 13
[2] Tetrahedron Letters, 1994, vol. 35, # 51, p. 9545 - 9548
[3] Patent: WO2006/51851, 2006, A1. Location in patent: Page/Page column 80
[4] Journal of the American Chemical Society, 1940, vol. 62, p. 1202

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