Piperazine, 1-(cyclopropylcarbonyl)-, Monohydrochloride Chemical Properties

Melting point:

175-179℃

storage temp. 

Inert atmosphere,Room Temperature

Water Solubility 

Soluble in water

form 

powder to crystal

color 

White to Orange to Green

InChI

InChI=1S/C8H14N2O.ClH/c11-8(7-1-2-7)10-5-3-9-4-6-10;/h7,9H,1-6H2;1H

InChIKey

WIHDAPMHNYYTOA-UHFFFAOYSA-N

SMILES

C(N1CCNCC1)(C1CC1)=O.Cl

CAS DataBase Reference

1021298-67-8

Safety Information

HS Code 

2933599590

Piperazine, 1-(cyclopropylcarbonyl)-, Monohydrochloride Usage And Synthesis

Uses

1-(Cyclopropylcarbonyl)piperazine Hydrochloride is a reagent used in the synthesis of Esaprazole analogs showing σ1 binding and neuroprotective properties in vitro.

Synthesis

The general procedure for the synthesis of cyclopropyl (piperazin-1-yl)methanone hydrochloride from tert-butyl 4-(cyclopropanecarbonyl)piperazine-1-carboxylate was as follows: to a stirring solution of tert-butyl 4-(cyclopropanecarbonyl)piperazine-1-carboxylate (3.7 g, 14.5 mmol) in methanol (15 mL) was added slowly at 0 °C a hydrochloric acid/methanol solution (15 mL, 3M). After addition, the reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure to afford cyclopropyl (piperazin-1-yl)methanone hydrochloride (2.74 g, 100% yield) as an off-white solid. The product was characterized by 1H-NMR (400 MHz, DMSO-d6): δ 0.71-0.76 (m, 4H), 1.96-2.03 (m, 1H), 3.04-3.16 (m, 4H), 3.69-4.08 (m, 4H), 9.58 (s, 2H); LC-MS (ESI) m/z: 155 (M + 1)+.

References

[1] Patent: US2010/35883, 2010, A1. Location in patent: Page/Page column 56
[2] Patent: WO2011/130661, 2011, A1. Location in patent: Page/Page column 102-103

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