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CAS No. : | 6269-89-2 | MDL No. : | MFCD00005961 |
Formula : | C10H13N3O2 | Boiling Point : | - |
Linear Structure Formula : | NH(CH2)4NC6H4NO2 | InChI Key : | VWOJSRICSKDKAW-UHFFFAOYSA-N |
M.W : | 207.23 | Pubchem ID : | 80447 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302+H312+H332-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 17 9-{4-[4-(4-nitro-phenyl)-piperazin-1-yl]-butyl}-9H-fluorene-9-carboxylic acid-(2,2,2-trifluoroethyl)-amide Prepared analogously to Example 2 b from 1-(4-nitro-phenyl)-piperazine and 9-(4-bromo-butyl)-9H-fluorene-9-carboxylic acid-(2,2,2-trifluoroethyl)-amide. Yield: 0.35 g (38.6% of theoretical). Melting point: 146 C. C30H31F3N4O3 (M=552.60). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.0 g (90%) | In N-methyl-acetamide; | Step 1 1.04 g (5.0 mmol) of N-(4-nitrophenyl)piperazine was dissolved in 5 ml of dimethylformamide. Sodium hydride (0.24 g, 6.0 mmol) was added to the reaction mixture in three portions under nitrogen atmosphere and cooling over a period of 10 min. After 30 min of stirring, 0.31 ml (6.0 mmol) of methyl iodide was added dropwise to the reaction mixture at 0 C. Stirring was continued for 1 h at room temperature, the reaction mixture was then evaporated to dryness, and purified by silica gel chromatography (methylene chloride:methanol:triethylamine 94:5:1) to yield 1.0 g (90%) of 1-methyl-4-(4-nitrophenyl)piperazine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; | 14.1 1-[(5-methoxy-1H-indol-3-yl)methylcarbonyl]-4-(4-nitrophenyl)-piperazine In a 100 ml flask, 1.62 g (10 mmoles) of 1.1'-carbonyl-diimidazole is added to a solution of 2.05 g (10 mmoles) of 5-methoxyindole-3-acetic acid in 10 ml of THF. After one hour of agitation at ambient temperature, a solution of 1-(4-nitrophenyl)piperazine in 10 ml of DMF is added dropwise. Agitation is continued for 15 hours. The reaction medium is then concentrated under vacuum and the evaporation residue is precipitated from 50 ml of an ethyl acetate/water mixture (1/1). After filtration, the solid is rinsed successively with 50 ml of water, 50 ml of ethyl acetate and 50 ml of dichloromethane. After drying under vacuum, a yellow powder is obtained with a yield of 91percent. Melting point: 239-240° C. NMR 1H (100 MHz, DMSO d6, delta): 10.90 (m, 1H, NH); 7.63 (m, 4H, Ph-NO2); 7.40-7.15 (m, 3H, indol); 6.87 (dd, 1H indol, Jotho=8.7 Hz, Jmeta=2.8 Hz); 3.90 (s, 2H, CH2-CO); 3.88 (s, 3H, OCH3); 3.79 (m, 4H, piperazine); 3.50 (m, 4H, piperazine). |
91% | 14.1) 1-[(5-methoxy-1H-indol-3-yl)methylcarbonyl]-4-(4-nitrophenyl)piperazine: In a 100 ml flask, 1.62 g (10 mmoles) of 1.1'-carbonyl-diimidazole is added to a solution of 2.05 g (10 mmoles) of 5-methoxyindole-3-acetic acid in 10 ml of THF. After one hour of agitation at ambient temperature, a solution of 1-(4-nitrophenyl)piperazine in 10 ml of DMF is added dropwise. Agitation is continued for 15 hours. The reaction medium is then concentrated under vacuum and the evaporation residue is precipitated from 50 ml of an ethyl acetate/water mixture (1/1). After filtration, the solid is rinsed successively with 50 ml of water, 50 ml of ethyl acetate and 50 ml of dichloromethane. After drying under vacuum, a yellow powder is obtained with a yield of 91percent. Melting point: 239-240° C. NMR 1H (100 MHz, DMSO d6, delta): 10.90 (m, 1H, NH); 7.63 (m, 4H, Ph-NO2); 7.40-7.15 (m, 3H, indol); 6.87 (dd, 1H indol, Jortho=8.7 Hz, Jmeta=2.8 Hz); 3.90 (s, 2H, CH2-CO); 3.88 (s, 3H, OCH3); 3.79 (m, 4H, piperazine); 3.50 (m, 4H, piperazine). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With sodium acetate; acetic acid; at 100℃; for 24h;Sealed tube; | 1.0 g of 1-(4-nitrophenyl)-piperazine (Compound A-1f), 12 mL of acetic acid was added to the sealed reactor, followed by the addition of 2.5 mL of hydrated formaldehyde, 1.0 g of sodium acetate;The reaction mixture was warmed to 100 C and stirred for 24 hours;The residue obtained was purified to give 1-(4-nitrophenyl)-4-methylpiperazine (A-f) (1.0 g, yield 94%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With tetrabutylammomium bromide; sodium carbonate; N-ethyl-N,N-diisopropylamine; In water; for 3h;Reflux; | In a round bottom flask, 5 cm3 water,0.453 g of <strong>[94088-46-7]2-fluoro-6-methoxybenzonitrile</strong> (0.003 mol), 0.621 g of 1-(4-nitrophenyl)piperazine (0.003 mol), 0.387 gof DIPEA (0.003 mol), 0.096 g of TBAB (0.0003 mol), and 0.318 g of Na2CO3(0.003 mol) was taken. Reaction was carried out at reflux for 3 h. Then reaction mixture was cooled and extracted with ethyl acetate. The product was purified by flash chromatography on silica using hexane-ethyl acetate mobile phase to afford 0.42 g 16 (42%). M.p.:160-164 C; 1H NMR (400 MHz, CDCl3):delta = 3.939 (s, 4H),3.649 (s, 4H), 3.953 (s, 3H), 6.630 (d, J = 4 Hz, 2H), 6.893(d, J = 8 Hz, 2H), 7.460 (t, J = 8 Hz, 1H), 8.165 (d, J = 8 Hz,2H) ppm; 13C NMR (100 MHz, CDCl3):delta = 46.1 (CH2), 46.8(CH2), 47.2 (CH2), 50.9 (CH2), 56.1 (OCH3), 104.8 (CCN),110.5 (CH), 112.9 (CH), 115.7 (CN), 129.9 (CH), 134.4(CH), 138.8 (CNO2), 154.7 (C), 156.6 (C), 163.0 (CO) ppm; IR (KBr): =nu 2886, 2215, 1594, 1480, 1322, 1600, 1508,1458, 1266 cm-1; ESI-MS: m/z = 339 (MH+). |
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