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[ CAS No. 16155-03-6 ]

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Chemical Structure| 16155-03-6
Chemical Structure| 16155-03-6
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CAS No. :16155-03-6 MDL No. :MFCD00101003
Formula : C11H15N3O2 Boiling Point : 369.5°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :221.26 g/mol Pubchem ID :2825198
Synonyms :

Safety of [ 16155-03-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 16155-03-6 ]

  • Upstream synthesis route of [ 16155-03-6 ]
  • Downstream synthetic route of [ 16155-03-6 ]

[ 16155-03-6 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 16155-03-6 ]
  • [ 16153-81-4 ]
YieldReaction ConditionsOperation in experiment
100% With palladium on activated charcoal; hydrogen In methanol at 20℃; General procedure: Afterwards, the obtained compound, 2a was hydrogenated. Pd/C (2.78mmol) was added to a stirred solution of 1-methyl-4-(2-methyl-4-nitrophenyl-piperazine (5.53mmol)) in methyl alcohol (15ml) in N2 atmosphere. Following this it was hydrogenated overnight by maintaining the reaction flask in an atmosphere of H2 gas (balloon). The resultant was filtered thorough celite plate and concentrated under vacuum. The crude product was purified with silica-gel column chromatography (5percentMeOH/DCM, 1percentNH3) to yield the desired product, 3a as a brown solid, 87percent yield.
98% With hydrogen In ethyl acetate at 20℃; for 18 h; Inert atmosphere 1-Methyl-4-(4-nitrophenyl)piperazine (111) (0.632 g, 2.86 mmol) was dissolved in EtOAc (45 mL) under an atmosphere of nitrogen and a slurry of 10percent Pd/C (0.200 g) in EtOAc (5 mL) was added. The resulting suspension was then stirred vigorously under an atmosphere of hydrogen at room temperature for 8 hours. The cataiyst was removed by filtration through Celite, which was washed with EtOAc (7x 0 mL) and the solvent was removed in vacuo to give the title compound (112) (0.537 g, 98percent yield) as a pink solid; H NMR (400 MHz, de-DMSO) δ 6.70 - 6.64 (m, 2H), 6.51 - 6.45 (m, 2H), 4.54 (s, 2H), 2.94 - 2.84 (m, 4H), 2.46 - 2.36 (m, 4H), 2.19 (s, 3H). LCMS Method C: rt 0.98 min; m/z 192.3 [M+H]+.
98% With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 18 h; Inert atmosphere 1-Methyi-4-(4-nitrophenyi)piperazine (111) (0.632 g, 2.86 mmol) was dissolved in EtOAc (45 mL) under an atmosphere of nitrogen and a slurry of 10percent Pd/C (0.200 g) in EtOAc (5 mL) was added. The resulting suspension was then stirred vigorously under an atmosphere of hydrogen at room temperature for 18 hours. The catalyst was removed by filtration through Ceiite, which was washed with EtOAc (7x10 mL) and the solvent was removed in vacuo to give the title compound (112) (0.537 g, 98percent yield) as a pink solid; 1H NMR (400 MHz, oV-DMSO) δ 6.70 - 6.64 (m, 2H), 6.51 - 6.45 (m, 2H), 4.54 (s, 2H), 2,94 - 2.84 (m, 4H), 2.46 - 2.36 (m, 4H), 2.19 (s, 3H). LCMS Method C: rt 0.98 min; m/z 192.3 [M+H]+.
95% With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 9 h; Inert atmosphere; Schlenk technique General procedure: The nitrophenyl analogue 7a–7e (7.5 mmol) was dissolved in ethanol (50 mL), and to this solution was added 10percent Pd/C (0.2 g). The reaction mixture was stirred at room temperature under an atmosphere of H2 for 9 h. After completion of the reaction, the resulting mixture was filtered through Celite. The filtrate was concentrated under high vacuum to afford the desired aniline derivatives 8a–8e.
92% With hydrogen In methanol at 20℃; Step b - 4-(4-methylpiperazin-1-yl)benzenamine; A solution of 1-methyl-4-(4-nitrophenyl)piperazine (1.03g, 4.66mmol) in MeOH (100ml) was hydrogenated at 2O0C at atmospheric pressure using an H-Cube (flow rate at 1ml/min and full hydrogen mode) using a Pd/C cartridge. The solvent was removed in vacuo to afford 4-(4-methylpiperazin-1-yl)benzenamine (0.82g, 4.29mmol, 92percent) as an off-white solid. 1H NMR (CDCI3) δ 2.37 (3H, s), 2.62 (4H, t), 3.09 (4H, t), 3.40 (2H, br. s), 6.65 (2H, d), 6.82 (2H, d). LCMS (1) Rt: 0.98min; m/z (ES+) 192.
91.1% With iron; ammonium chloride In ethanol for 5 h; Reflux In 50ml single-necked flask M-30.60g (0.27mmol), ammonium chloride 0.46g (1.34mmol) and 70percent ethanol 25ml, was added portionwise stir reduced iron powder 0.46g (0.80mmol), was heated to reflux. 5After h TLC showed the starting material is no longer remaining. Hot filtration, the filtrate was evaporated under reduced pressure, water was added, extracted with ethyl acetate (15ml × 3), the combined organic phase was washed twice with saturated brine, dried over anhydrous MgSO 4. After concentration under reduced pressure column chromatography (PE:EA = 1:1) was a light brown liquid 0.47g, yield 91.1percent.
89% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; To a 500 mL reaction flask,Adding 13.12 g of compound 20,Add 200 mL of methanol,And 1.45 g of 10percent Pd / C,Through the hydrogen, room temperature reaction overnight,The reaction ends,The palladium-carbon was removed by filtration,The filtrate was concentrated,The residue was purified by column chromatography (MeOH: DCM = 10: 1)To give 9.9 g of a gray solid 7-2. Yield 89percent.
83.2% With palladium 10% on activated carbon In methanol at 20℃; for 5 h; 1.0 g of 4- (4-methylpiperazine) nitrobenzene (compound 6) was dissolved in 20 mL of methanol, Slowly added with stirring catalytic amount of 10percent Pd / C, at room temperature for 5h. The reaction solution was suction filtered to remove Pd / C,Wash the filter cake with methanol. The filtrate was depressurized to remove methanol and extracted with ethyl acetate (30 mL × 3). The organic phases were combined,Saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, the filtrate was concentrated under reduced pressure,0.72 g of 4- (4-methylpiperazine) aniline (Compound 7) was isolated by column chromatography, and the reaction yield was 83.2percent.
80% With iron; ammonium chloride In ethanol for 8 h; Reflux Add in 100ml single neck bottleM-3 (2.00 g, 9.04 mmol),Ammonium chloride (2.42g, 45.2mmol)And 70percent ethanol 25ml,Stir well and add in batchesReduced iron powder (1.52g, 27.1mmol),Heat to reflux.After 8 h, TLC showed no residue of starting material.Hot and suction filtration,The filtrate was distilled off under reduced pressure.Crude column chromatography (PE: EA = 1: 1)A pale yellow liquid of 1.38 g was obtained in a yield of 80.0percent.
75% With ammonium hydroxide; sodium dithionite In water for 0.25 h; Reflux General procedure: To a solution of 1-(substituted) 4-nitrobenzene IVa,b,e,f(0.01 mol) in NH4OH (20 mL, 30percent), a solution of sodium dithionite(7 g, 0.04 mol) in water (30 mL) was quickly added, the reactionmixture was refluxed for 15 min. After cooling, the crude productwas filtered, washed and crystallized from methylene chloride toyield target compounds Va,b,e,f. 4-(4-Methylpiperazin-1-yl) aniline Ve
Yield 75percent as off white acicular solid, mp 90 °C, (as reported) [62,67,68].
70% With hydrogenchloride; tin In chloroform; waterReflux General procedure: Concisely,1-(4-Nitro phenyl)-4-substitued piperazine derivatives (1-18) were refluxed for 3-4 h in chloroform (20 ml) with theSn/HCl solution. The solution was prepared before by dissolving tin (15mM) in30ml Con. HCl. The reaction mixture was cooled under tap water and neutralizedwith 15percent NaOH solution. The resulting compound was extracted with ethylacetate. The organic layer was dried over anhydrous sodium sulphate andevaporated under reduced pressure to afford of 4-(4-substitutedpiperazin-1-yl)-phenylamine derivatives (19-36)as solid compounds.
64% With hydrogen In methanol l-Methyl-4-(4-nitro-phenyl)-piperazine (200mg) was hydro genated over 10percent Pd-C (20mg) in methanol (20ml) at atmospheric pressure until no further gas uptake was observed. The reaction mixture was then filtered over celite and concentrated to give a crude solid. Column chromatography over silica gel using 4percent methanol in dichloromethane gave 4-(4-methyl-piperazin-l-yl)-phenylamine (HOmg, 64percent) as solid.
7.67 g With 10% palladium on activated carbon; hydrogen In ethanol at 20℃; The mixture of 1-methyl-4-(4-nitro-phenyl)-piperazine (10.2 g, 45.0 mmol) and 10percent Pd/C (0.5g) in EtOH (350 mL) was stirred at room temperature under H2. After the completion of the reaction, the mixture was filtered through celite and purified with column chromatography (dichloromethane : MeOH : n-hexane = 10 : 1 : 1) to afford 4-(N-methyl-piperazin-1-yl)-phenylamine 9 (7.67 g, 39.8 mmol): 1H NMR (200 MHz, CDCl3) δ 2.34 (s, 3H, NCH3), 2.55 - 2.60 (m, 4H, NCH2 x 2), 3.04 - 3.09 (mz, 4H, NCH2 x 2), 3.41 (br s, 2H, NH2), 6.64 (m, 2H, ArH), 6.80 (m, 2H, ArH); MS(EI) m/e 191 [M+].
2.4 g With palladium 10% on activated carbon; hydrogen In ethyl acetate at 80℃; for 12 h; General procedure: To a mixture of 5a (2.13g, 10mmol) in dry ethyl acetate was added 10percent Pd/C (0.5g), following the reaction mixture was stirred under hydrogen gas at 80°C for 12h. The reaction mixture was concentrated in vacuo and the crude product was purified by column chromatography (dichloromethane/methanol 15:1 by volume) to give 4-morpholinyl aniline 6a (1.5g, yield 85percent).
250 mg With iron; ammonium chloride In methanol; water at 100℃; General procedure: The compound S1 (261 mg, 1.25 mmol), iron powder (210 mg, 4.76 mmol, 3 equiv.) and ammonium chloride (335 mg, 6.27 mmol, 5 equiv.) were dissolved in methanol : water (2 : 1, 15 mL). The reaction mixture was heated at 100 °C overnight, cooled to RT, filtered through celite and the solvent was reduced under vacuum. The condensed mixture was extracted with DCM, washed with brine, dried with sodium sulfate and all solvent was evaporated to furnish the condensed residue, which was purified by flash chromatography (elution system - EA/Hexane = 1 : 1 ) to obtain the title compound (245 mg, 1.43 mmol).

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  • 2
  • [ 16155-03-6 ]
  • [ 16153-81-4 ]
Reference: [1] Patent: US2001/46991, 2001, A1,
  • 3
  • [ 16155-03-6 ]
  • [ 1357470-29-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 3, p. 578 - 599
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