2-[4-(4-NITROPHENYL)PIPERAZINO]-1-ETHANOL Chemical Properties

Melting point:

97-99°C

Boiling point:

445.6±45.0 °C(Predicted)

Density 

1.258±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

14.96±0.10(Predicted)

form 

Solid

Safety Information

HazardClass 

IRRITANT

2-[4-(4-NITROPHENYL)PIPERAZINO]-1-ETHANOL Usage And Synthesis

Synthesis

To a stirred suspension of anhydrous dimethyl sulfoxide (10 mL) of 1-fluoro-4-nitrobenzene (2 g, 14.17 mmol) and potassium carbonate (3.92 g, 28.3 mmol) was slowly added 2-(piperazin-1-yl)ethanol (2.089 mL, 17.01 mmol). The reaction mixture was heated and stirred at 80°C for 16 hours. After completion of the reaction, it was cooled to room temperature and the mixture was poured into water (100 mL) and extracted with ethyl acetate (30 mL). The aqueous layer was separated and a second extraction was performed with ethyl acetate (2 x 30 mL). All organic phases were combined and concentrated under reduced pressure to remove the solvent. The concentrated residue was ground in water (100 mL) to precipitate a solid. The solid product was collected by vacuum filtration and dried under vacuum with a stream of nitrogen for 16 h to afford the target compound 2-[4-(4-nitrophenyl)piperazine]-1-ethanol (3.45 g, 97% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 8.11 (d, 2H), 6.82 (d, 2H), 3.68 (t, 2H), 3.44 (t, 4H), 2.67 (t, 4H), 2.62 (t, 2H), 2.55 (br s, 1H).Results of the analysis by LCMS (Method C): retention time (RT) = 0.45 min, m/z = 252 [M + H]+.

References

[1] Patent: WO2015/92431, 2015, A1. Location in patent: Page/Page column 236
[2] Patent: WO2015/27222, 2015, A2. Location in patent: Paragraph 0322
[3] Patent: WO2012/59932, 2012, A1. Location in patent: Page/Page column 112-113
[4] Patent: WO2016/138527, 2016, A1. Location in patent: Paragraph 00212
[5] Journal of Medicinal Chemistry, 2005, vol. 48, # 7, p. 2371 - 2387