N-4-Boc-2-piperazinecarboxylic acid Chemical Properties

Melting point:

231-239 °C

Boiling point:

371.8±37.0 °C(Predicted)

Density 

1.193±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

2.20±0.20(Predicted)

form 

powder or crystals

Appearance

White to off-white Solid

Water Solubility 

Slightly soluble in water.

CAS DataBase Reference

128019-59-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-43-36

Safety Statements 

26-36/37/39-36/37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29335990

N-4-Boc-2-piperazinecarboxylic acid Usage And Synthesis

Chemical Properties

White powder

Uses

As active pharmaceutical drugs and intermediates possess different biological activities.

Synthesis

General procedure for the synthesis of 4-Boc-piperazine-2-carboxylic acid from di-tert-butyl dicarbonate and piperazine-2-carboxylic acid dihydrochloride: sodium bicarbonate (3.1 g, 36.9 mmol) was added to a stirred suspension of piperazine-2-carboxylic acid (5 g, 24.6 mmol) in 1,4-dioxane and water (1:1, 100 mL) under nitrogen protection. Subsequently, di-tert-butyl dicarbonate (5.6 mL, 24.6 mmol) was added slowly at 0 °C. The reaction mixture was gradually warmed to room temperature and stirred continuously for 16 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming complete consumption of the raw materials, the reaction mixture was diluted with water (50 mL) and extracted with ether (2 x 100 mL). The aqueous phase was acidified with 2N hydrochloric acid solution and then extracted with n-butanol. The organic phases were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to afford the target compound 4-Boc-piperazine-2-carboxylic acid (5 g, 88% yield) as a white solid.1H-NMR (500 MHz, DMSO-d6): δ 10.18 (broad peak, 1H), 4.08 (broad peak, 1H), 3.81-3.71 (multiple peaks, 2H), 3.63 (triple peak, J=6.5Hz, 1H), 3.17-3.15 (multiple peaks, 2H), 2.91-2.86 (multiple peaks, 1H), 1.36 (single peak, 9H), 1.31-1.26 (multiple peaks, 0.5H), 0.87-0.84 (multiple peaks, 0.5H). lcms (esi): m/z 229.0 [M+H]+.

References

[1] Patent: WO2018/26782, 2018, A1. Location in patent: Page/Page column 30-31
[2] Journal of Medicinal Chemistry, 2000, vol. 43, # 3, p. 369 - 380

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