1-Boc-3-oxopiperazine Chemical Properties

Melting point:

156-160 °C(lit.)

Boiling point:

359.1±35.0 °C(Predicted)

Density 

1.129±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

15.01±0.20(Predicted)

form 

Crystalline Powder

color 

White to off-white

InChI

InChI=1S/C9H16N2O3/c1-9(2,3)14-8(13)11-5-4-10-7(12)6-11/h4-6H2,1-3H3,(H,10,12)

InChIKey

FCMLWBBLOASUSO-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCNC(=O)C1

CAS DataBase Reference

76003-29-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

1-Boc-3-oxopiperazine Usage And Synthesis

Chemical Properties

White to off-white solid

Uses

4-Boc-2-oxopiperazine is used in the synthesis of renin inhibitors. Also used in the synthesis of isoindoline inhibitors of dipeptidyl peptidases.

Synthesis

GENERAL STEPS: Piperazin-2-one (1.037 g, 10.4 mmol) was dissolved in 52 mL of dichloromethane, followed by the addition of di-tert-butyl dicarbonate (Boc2O, 2.5 g, 11.4 mmol). The reaction mixture was stirred at room temperature for 3 h before complete consumption of piperazin-2-one was confirmed by thin layer chromatography (TLC) monitoring. Upon completion of the reaction, the reaction mixture was diluted with dichloromethane and the organic layer was washed with deionized water. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 1-Boc-3-piperazinone (product 33) in quantitative yield as a white solid. The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3): δ 1.48 (s, 9H), 3.35-3.44 (m, 2H), 3.64 (t, J = 5 Hz, 2H), 4.10 (s, 2H), 6.41 (br s, 1H).

References

[1] Patent: WO2005/117904, 2005, A2. Location in patent: Page/Page column 407
[2] Patent: WO2011/41713, 2011, A2. Location in patent: Page/Page column 147-148
[3] European Journal of Medicinal Chemistry, 2015, vol. 101, p. 218 - 235
[4] Patent: WO2006/72350, 2006, A1. Location in patent: Page/Page column 37
[5] Patent: WO2006/72353, 2006, A1. Location in patent: Page/Page column 30

1-Boc-3-oxopiperazine(76003-29-7)Related Product Information

• tert-Butyl chloroacetate
• N-Aminoethylpiperazine
• tert-Butyl acetoacetate
• Cyhalofop-butyl
• Piperazine
• tert-Butyl bromoacetate
• butyl rubber
• Piperacillin
• Buprofezin
• tert-Butanol
• RESMETHRIN
• 2-Butoxyethanol
• 2-Ethylhexyl ferulate
• PIPERAZINE HEXAHYDRATE
• Butyl acetate
• 2-Piperazinone
• Piperazine citrate
• Butyl acrylate