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| | 4-(4-(4-Nitrophenyl)-1-piperazinyl)phenol Basic information |
| Product Name: | 4-(4-(4-Nitrophenyl)-1-piperazinyl)phenol | | Synonyms: | 1-(4-HYDROXYPHENYL)-4-(4-NITROPHENYL)-PIPERAZINE;4-(4-(4-Nitrophenyl)-1-piperazinyl)phenol;4-(4-(4-nitrophenyl)piperazin-1-yl)phenol;4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenol;4-(4-(4-Nitrophenyl)-1-piperazinyl)phenol Itraconazole interMediate;Posaconazole impurity NPPY;1-(4-Nitrophenyl)-4-(4-hydroxyphenyl)piperazine;Phenol, 4-[4-(4-nitrophenyl)-1-piperazinyl]- | | CAS: | 112559-81-6 | | MF: | C16H17N3O3 | | MW: | 299.32 | | EINECS: | 601-189-8 | | Product Categories: | Heterocyclic Compounds | | Mol File: | 112559-81-6.mol |  |
| | 4-(4-(4-Nitrophenyl)-1-piperazinyl)phenol Chemical Properties |
| Melting point | >90°C (dec.) | | Boiling point | 540.8±50.0 °C(Predicted) | | density | 1.317±0.06 g/cm3(Predicted) | | storage temp. | Sealed in dry,Room Temperature | | solubility | DMSO (Slightly, Heated) | | pka | 12.18±0.30(Predicted) | | form | Solid | | color | Yellow to Brown | | InChI | InChI=1S/C16H17N3O3/c20-16-7-5-14(6-8-16)18-11-9-17(10-12-18)13-1-3-15(4-2-13)19(21)22/h1-8,20H,9-12H2 | | InChIKey | BNHYDULILNJFFY-UHFFFAOYSA-N | | SMILES | C1(O)=CC=C(N2CCN(C3=CC=C([N+]([O-])=O)C=C3)CC2)C=C1 | | CAS DataBase Reference | 112559-81-6(CAS DataBase Reference) |
| | 4-(4-(4-Nitrophenyl)-1-piperazinyl)phenol Usage And Synthesis |
| Uses | 4-[4-(4-Nitrophenyl)-1-piperazinyl]phenol is a key intermediate in the synthesis of triazole medicines, such as itraconazole (I937500), which are used in curing deep department fungal infections. Inhibitor of endothelial cell proliferation. | | Synthesis | Under nitrogen protection, 420 g (2.36 mol) of 4-(1-piperazinyl)phenol, 520.6 g (3.30 mol) of 4-chloronitrobenzene, and 457.5 g (3.54 mol) of N,N-diisopropylethylamine (Huenig's base) were suspended in 1260 mL of N-methylpyrrolidone. The mixture was heated to 120-125°C until a clarified solution was formed. This temperature was maintained and the progress of the reaction was monitored by HPLC. Upon completion of the reaction (5-7 hr), the reaction solution was cooled to 75-80°C. 6.3 L of isopropanol was slowly added to the reaction mixture over a period of about 30 min while maintaining the temperature at 75-80°C (with slight heating if necessary). At the end of the addition, the product began to precipitate as yellow crystals. The suspension was cooled to 20-25°C and stirred at this temperature overnight. Subsequently, the suspension is further cooled to -10 to -5°C and stirred for 30 minutes. The product was collected by filtration and washed sequentially with 1.7 L of isopropanol and 5 x 840 mL of warm water (35-40°C). Finally, the product was dried under vacuum at 50°C (accompanied by a slight stream of nitrogen) to constant weight. The yield was 96% and the purity as determined by HPLC was 93%, which corresponded to the standard. | | References | [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 8, p. 3635 - 3649
[2] Patent: EP1230231, 2005, B1. Location in patent: Page/Page column 4
[3] Journal of Medicinal Chemistry, 2011, vol. 54, # 20, p. 7363 - 7374
[4] Patent: WO2018/45106, 2018, A1. Location in patent: Paragraph 00131
[5] Patent: WO2018/45104, 2018, A1. Location in patent: Paragraph 00156 |
| | 4-(4-(4-Nitrophenyl)-1-piperazinyl)phenol Preparation Products And Raw materials |
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