1,4-BIS(N-BOC)PIPERAZINE-2-CARBOXYLIC ACID Chemical Properties

Melting point:

142-148°C

Boiling point:

443.9±40.0 °C(Predicted)

Density 

1.200±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

3.70±0.20(Predicted)

form 

solid

Appearance

White to off-white Solid

InChIKey

IIZGWFQKLVCLLA-UHFFFAOYSA-N

Safety Information

Hazard Codes 

Xi

Risk Statements 

36-43

Safety Statements 

26-36/37

WGK Germany 

3

HS Code 

29335990

1,4-BIS(N-BOC)PIPERAZINE-2-CARBOXYLIC ACID Usage And Synthesis

Chemical Properties

White powder

Synthesis

General procedure for the synthesis of 1,4-bis-BOC-2-piperazinecarboxylic acid from 2-piperazinecarboxylic acid and di-tert-butyl dicarbonate: In a 1 L round bottom flask, 15.76 g NaOH (394 mmol) was dissolved in 390 mL of water, followed by the addition of 20 g of 2-piperazinecarboxylic acid (98 mmol) in batches to obtain a colorless solution. A solution of 50 mL of Boc2O (215 mmol) dissolved in 1,4-dioxane was added slowly and dropwise while the temperature was maintained below +5 °C. Upon completion of the reaction, the mixture was cooled to +5 °C and the pH was subsequently adjusted to 3 with 3N HCl. The suspension was extracted with 300 mL of ethyl acetate (AcOEt), the organic phases were combined and dried over sodium sulfate. After vacuum evaporation, 22.7 g of white solid product was obtained. The aqueous phase was acidified with 3N HCl to pH=3 and then extracted with 2×100mL ethyl acetate (AcOEt), and the organic phases were similarly dried with sodium sulfate and then vacuum evaporated to give a second batch of 7.9g of product. The two batches of product were combined to give the final 1,4-bis-BOC-2-piperazinecarboxylic acid (30.6 g, 94% yield). The product was confirmed by 1H-NMR (400 MHz, DMSO-d6): δ 1.33 (18H, m), 2.70-4.50 (8H, m), 12.9 (1H, s); the mass spectrum (ES) showed m/z 330 [M+H]+.

References

[1] Patent: WO2008/148853, 2008, A1. Location in patent: Page/Page column 157-158
[2] Patent: US2014/288045, 2014, A1. Location in patent: Paragraph 0531
[3] Angewandte Chemie - International Edition, 2018,
[4] Angew. Chem., 2018, vol. 130, # 44, p. 14768 - 14773,6
[5] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 23, p. 4241 - 4244

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