tert-Butyl 4-(2-fluoro-4-nitrophenyl)piperazine-1-carboxylate Chemical Properties

Melting point:

153-155 °C(Solv: ethyl ether (60-29-7))

Boiling point:

453.5±45.0 °C(Predicted)

Density 

1.270±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

Solid

pka

0.11±0.10(Predicted)

Appearance

Light yellow to yellow Solid

CAS DataBase Reference

154590-34-8

Safety Information

HS Code 

2933599590

tert-Butyl 4-(2-fluoro-4-nitrophenyl)piperazine-1-carboxylate Usage And Synthesis

Synthesis

General procedure for the synthesis of tert-butyl 4-(2-fluoro-4-nitrophenyl)piperazine-1-carboxylate: 1. 1-(2-fluoro-4-nitrophenyl)piperazine (12.5 g, 55.8 mmol) was dissolved in 1,4-dioxane (108 mL) under cooling conditions in an ice bath. 2. 1N sodium hydroxide solution (54 mL) and di-tert-butyl dicarbonate (14 mL, 61.38 mmol) were added sequentially to the above solution. 3. The temperature of the reaction mixture was adjusted to 25-35°C and stirred continuously for 0.5 hours. 4. Upon completion of the reaction, the mixture was poured into ice-cold water (200 mL) and a yellow precipitate was precipitated. 5. The precipitate was collected by filtration through a Büchner funnel to afford the target product tert-butyl 4-(2-fluoro-4-nitrophenyl)piperazine-1-carboxylate (18.0 g, 99% yield). Product characterization data: 1H NMR (CDCl3): δ 8.01-7.88 (m, 2H), 6.93 (t, J = 8.6 Hz, 1H), 3.61 (t, J = 4.9 Hz, 4H), 3.24 (t, J = 4.9 Hz, 4H), 1.49 (s, 9H). IR (KBr, cm-1): 3119, 1692, 1605, 1512. CI-MS (m/z): 326 (M++1), 270, 240, 226, 195, 183, 131, 96.

References

[1] Patent: WO2005/82892, 2005, A2. Location in patent: Page/Page column 61
[2] Patent: CN107033095, 2017, A. Location in patent: Paragraph 0085; 0086
[3] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 19, p. 4261 - 4267
[4] Patent: US2004/220194, 2004, A1. Location in patent: Page 13; 14
[5] Patent: US2005/239795, 2005, A1. Location in patent: Page/Page column 18

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