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CAS No. : | 182618-86-6 | MDL No. : | MFCD02187326 |
Formula : | C15H21N3O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MGYCIJUTYLUYJM-UHFFFAOYSA-N |
M.W : | 307.35 | Pubchem ID : | 3380696 |
Synonyms : |
|
Num. heavy atoms : | 22 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.53 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 92.46 |
TPSA : | 78.6 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.38 cm/s |
Log Po/w (iLOGP) : | 2.77 |
Log Po/w (XLOGP3) : | 2.53 |
Log Po/w (WLOGP) : | 1.89 |
Log Po/w (MLOGP) : | 1.23 |
Log Po/w (SILICOS-IT) : | -0.48 |
Consensus Log Po/w : | 1.59 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.21 |
Solubility : | 0.189 mg/ml ; 0.000615 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.83 |
Solubility : | 0.0458 mg/ml ; 0.000149 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.44 |
Solubility : | 1.1 mg/ml ; 0.00359 mol/l |
Class : | Soluble |
PAINS : | 1.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.63 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
90% | With trifluoroacetic acid In dichloromethane at 20℃; for 1 h; | Step: 5bSynthesis of l-(4-Nitro-phenyl)-piperazine.Procedure:TFA (6ml) and was added to a solution of 4-(4-Nitro-phenyl)-piperazine-l -carboxylic acid tert-butyl ester (2g, 0.07166mol) in DCM (20ml) and stirred for lhr at RT. The reaction was monitored by TLC (10percent MeOH: CHC13). The reaction mixture was concentrated and the residue was washed with water and and dried at reduced pressure to afford a 2.2g (90percent yield) of solid l-(4-Nitro-phenyl)-piperazine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With potassium carbonate In N,N-dimethyl-formamide at 50℃; | To a solution of terf-butyl-piperazine (1 eq) and 4-fluoro-nitrobenzene (1.1 eq) in DMF (0.43 M), K2CO3 (1.1 eq) was added. The mixture was heated to 50 °C with stirring overnight. At this time the reaction was allowed to cool to RT and partitioned between EtOAc and IN aqueous HCl. The aqueous fraction was extracted with EtOAc and the combined organics washed with brine, before being dried over Na2SO4, filtered and evaporated in vacuo to afford the title compound as yellow solid (97 percent); MS (ES+) m/z 308 (M+H)+. |
95% | With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 18 h; | To a solution of 1-fluoro-4-nitrobenzene (5 g, 35.43 mmol) and tert-butyl piperazine-1- carboxylate (6.6 g, 35,43 mmol) in DMF (100 mL) was added potassium carbonate (14.7g, 106.36 mmol) and the mixture was stirred at 50 °C for 18 h, then allowed to cool to room temperature and concentrated under reduced pressure. The oily residue was washed with diethyl ether (3x) to give tert-butyl 4-(4-nitrophenyl)piperazine-1-carboxylate as a yellow solid (8.2 g, 95percent). ‘HNMR(400 MFIz, Chloroform-d) ppm 1.48 (s, 9 H) 3.38- 3.45(m,4H)3.56-3.63 (m,4H)6.75 -6.86(m,2H)8.07-8.20(m,2H). C15H21N304MS m/z 308.1 (M+H) |
85.3% | With potassium carbonate In N,N-dimethyl-formamide at 80℃; | Compound 18 (10.0 g, 70.87 mmol) was added to the reaction flask, respectively,Compound 36 (15.84 g, 85.05 mmol)Dissolved in DMF,K2CO3 (15.67 g, 113.39 mmol) was added,80 ° C under the conditions of reaction,TLC tracking, to be completely complete,The reaction system is poured into ice water,There is a yellow solid precipitation,Filter the solid, beat with ether,18.58 g of compound 40 was dried,Yield: 85.3percent. |
77% | With N-ethyl-N,N-diisopropylamine In ethyl acetate | 4-(4-Nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester 4-Fluoronitrobenzene (4.8 g, 34 mmol) was dissolved in ethyl acetate (25 mL). Piperazine-1-carboxylic acid tert-butyl ester (6.7 g, 36 mmol) and N,N-diisopropylethylamine (6.3 mL, 36 mmol) were added and the mixture was stirred at 65° C. for five days and cooled to room temperature. Ether (100 mL) was added and the combined mixture was washed with water (25 mL) and brine (25 mL), dried (Na2SO4), filtered and concentrated under vacuum. The residue was triturated with hexane to yield a bright yellow solid (8 g, 77percent). |
77% | With N-ethyl-N,N-diisopropylamine In ethyl acetate | 4-(4-Nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester. 4-Fluoronitrobenzene (4.8 g, 34 mmol) was dissolved in ethyl acetate (25 mL). Piperazine-1-carboxylic acid tert-butyl ester (6.7 g, 36 mmol) and N,N-diisopropylethylamine (6.3 mL, 36 mmol) were added and the mixture was stirred at 65° C. for five days and cooled to room temperature. Ether (100 mL) was added and the combined mixture was washed with water (25 mL) and brine (25 mL), dried (Na2SO4), filtered and concentrated under vacuum. The residue was triturated with hexane to yield a bright yellow solid (8 g, 77percent). |
77% | With N-ethyl-N,N-diisopropylamine In ethyl acetate | 4-(4-Nitro-phenyl)-piperazine-1-carboxylic acid Tert-butyl Ester 4-Fluoronitrobenzene (4.8 g, 34 mmol) was dissolved in ethyl acetate (25 mL). Piperazine-1-carboxylic acid tert-butyl ester (6.7 g, 36 mmol) and N,N-diisopropylethylamine (6.3 mL, 36 mmol) were added and the mixture was stirred at 65° C. for five days and cooled to room temperature. Ether (100 mL) was added and the combined mixture was washed with water (25 mL) and brine (25 mL), dried (Na2SO4), filtered and concentrated under vacuum. The residue was triturated with hexane to yield a bright yellow solid (8 g, 77percent). |
48% | With potassium carbonate In N,N-dimethyl-formamide at 80℃; | Step: 5aSynthesis of 4-(4-Nitro-phenyl)-piperazine-l-carboxylic acid tert-butyl ester.Procedure:K2C03 (2.7g, 0.0194mol) was added to 1 -Fluoro-4-nitro-benzene (2.5g, 0.0177mol) and Piperazine-1 -carboxylic acid tert-butyl ester (3.2g, 0.0177mol) in DMF (10ml) at 80°C. The reaction was monitored by the TLC (30percent EtOAc: hexane). The resultant was cooled to RT and precipitated by the addition of ice. The precipitate was collected and dried at reduced pressure to afford 2.6g (48percent yield) of 4-(4-Nitro-phenyl)-piperazine-l- carboxylic acid tert- buyl ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With N-ethyl-N,N-diisopropylamine In 1,4-dioxane | A. 4-(4-Nitrophenyl)-1-piperazinecarboxylic acid, 1,1-dimethylethyl Ester 1-(4-Nitrophenyl)piperazine (20 g, 96.5 mmol) (Acros Organics) was dissolved in dioxane (300 mL), and diisopropylethylamine (13.7 g, 106 mmol) (Aldrich) was added. To the solution was added di-tert-butyl dicarbonate (21 g, 96.6 mmol). After stirring overnight, the mixture was poured into water (1 L) and stirred for 10 minutes. The aqueous layer was extracted with ethyl acetate (2*500 mL) and the combined organic extracts were dried over MgSO4, filtered, and evaporated in vacuo. The residue was recrystallized from a mixture of ethyl acetate/hexane to provide 4-(4-nitrophenyl)-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester (22.7 g, 77percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With triethylamine In dichloromethane at 20℃; for 20 h; | 4-(4'-Nitrophenyl)piperazine hydrochloride (5.00 g, 20.5 mmol) was dissolved in DCM (100 mL) and treated with triethylamine (7.15 mL, 51 .3 mmol) followed by Boc anhydride (4.93 g, 22.6 mmol) and the reaction was stirred at room temperature for 20 hours. To the mixture was added water (100 mL) and DCM (70 mL) and the layers were separated. The aqueous layer was extracted with DCM (100 mL), the organics were combined and washed with brine (100 mL), dried (Na2S04), filtered and concentrated in vacuo to give a yellow-orange solid. The product was purified by silica gel chromatography (Biotage Isolera, 120 g Si cartridge, 0-100percent EtOAc in petroleum benzine 40-60 °C) to give the title compound (11) (4.895 g, 78percent yield) as a yellow solid; 1H NMR (400 MHz, de-DMSO) δ 8.10 - 8.04 (m, 2H), 7.04 - 6.97 (m, 2H), 3.48 (m, 8H), 1.42 (s, 9H). LCMS Method C: rt 6.13 min; m/z 208.2 [M- Boc+2Hf. |
78% | With triethylamine In dichloromethane at 20℃; for 20 h; | 4-(4'-Nitrophenyl)piperazine hydrochloride (5.00 g, 20.5 mmo) was dissolved in DCM (100 mL) and treated with triethyamine (7.15 mL, 51.3 mmol) followed by Boc anhydride (4.93 g, 22.6 mmol) and the reaction was stirred at room temperature for 20 hours. To the mixture was added water (100 mL) and DCM (70 mL) and the layers were separated. The aqueous layer was extracted with DCM (100 mL), the organics were combined and washed with brine (100 mL), dried (Na2S04), filtered and concentrated in vacuo to give a yelow-orange solid. The product was purified by silica gel chromatography (Biotage Isolera, 120 g Si cartridge, 0-100percent EtOAc in petroleum benzine 40-60 °C) to give the title compound (//) (4.895 g, 78percent yield) as a yellow solid; 1H NMR (400 MHz, o-DMSO) δ 8.10 - 8.04 (m, 2H), 7.04 - 6.97 (m, 2H), 3.48 (m, 8H), 1.42 (s, 9H). LC S Method C: rt 8.13 min; m/z 208.2 [M- Boc+2H]4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With hydrogen In methanol; ethyl acetate for 2 h; | Pd on C 10percent (0.3 percent p/p) was added to a solution of terf-butyl 4-(4-nitrophenyl)piperazine-l-carboxylate (1 eq) in a mixture (1 : 1 ratio) MeOH : EtOAc (0.03 M). The atmosphere in the reaction vessel was charged with H2 (1 arm.) and the reaction stirred vigorously for 2 h. At this time, the reaction mixture was filtered through a pad of celite and concentrated in vacuo to afford the title compound (quant); MS (ES+) m/z 278 (M+H)+ |
99% | With hydrogen In ethyl acetate at 20℃; for 42 h; Inert atmosphere | ferf-Butyl 4-(4-nitrophenyl)piperazine-1-carboxylate (11) (3.24 g, 10.5 mmol) was dissolved in EtOAc (90 mL) under an atmosphere of nitrogen and a slurry of 10percent Pd/C (0.500 g) in EtOAc (10 mL) was added. The resulting suspension was then stirred vigorously under an atmosphere of hydrogen at room temperature for 42 hours. The catalyst was removed by filtration through Celite, which was washed with EtOAc (7 x 10 mL) and the solvent was removed in vacuo to give the title compound (12) (2.92 g, 99 percent yield) as a pale pink solid; 1H NMR (400 MHz, oVDMSO) δ 6.72 - 6.66 (m, 2H), 6.52 - 6.45 (m, 2H), 4.60 (s, 2H), 3.44 - 3.39 (m, 4H), 2.87 - 2.79 (m, 4H), 1.41 (s, 9H). LCMS Method C: rt 4.40 min; m/z 278.2 [M+H]+. |
99% | With palladium 10% on activated carbon; hydrogen In ethanol; ethyl acetate at 20℃; for 42 h; Inert atmosphere | tert-Butyl 4-(4-nitrophenyl)piperazine-1-carboxyiate (11) (3.24 g, 10.5 mmol) was dissolved in EtOAc (90 mL) under an atmosphere of nitrogen and a slurry of 10percent Pd/C (0.500 g) in EtOAc (10 mL) was added. The resulting suspension was then stirred vigorously under an atmosphere of hydrogen at room temperature for 42 hours. The catalyst was removed by filtration through Celite, which was washed with EtOAc (7 x 10 mL) and the solvent was removed in vacuo to give the title compound (12) (2.92 g, 99 percent yield) as a pale pink solid; 1H N R (400 MHz, afe-DMSO) δ 6.72 - 6.66 (m, 2H), 6.52 - 6.45 (m, 2H), 4.60 (s, 2H), 3.44 - 3.39 (m, 4H), 2.87 - 2.79 (m, 4H), 1.41 (s, 9H). LCMS Method C: rt 4.40 min; m/z 278.2 [M+H]+. |
98% | With hydrogen In ethanol | 4-(4-Nitrophenyl)-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester (20 g, 65 mmol) was dissolved in anhydrous ethanol (250 mL) and 10percent Pd/C (1.8 g) was added. The mixture was stirred for 1.5 h under 10 psi of hydrogen and filtered through a Celite pad. The pad was washed with ethyl acetate (3*100 mL) and the combined solution was evaporated in vacuo to yield 4-(4-amino-phenyl)-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester (18 g, 98percent yield). |
97% | With palladium 10% on activated carbon; hydrogen In methanol for 16 h; | A solution of tert-butyl 4-(4-nitrophenyl)piperazine- 1 -carboxylate (8.2 g, 26.68 mmol) inMeOH (100 mL) was purged using nitrogen and reduced pressure. Palladium on charcoal(10percent wet) was added and the mixture was hydrogenated (50 psi) for 16 h. The reaction mixture was filtered through diatomaceous earth and concentrated under reduced pressure to give tert-butyl 4-(4-aminophenyl)piperazine-1-carboxylate (7.4 g, 97percent) as a dark blue oil used directly into the next step. C15H23N302 MS m/z 277.9 (M+H). |
73.8% | With palladium on activated charcoal; hydrogen In methanol at 20℃; | To the reaction flask was added compound 40 (17.57 g, 63.39 mmol)Soluble in methanol,Add 1.7 g of Pd / C,Catalytic hydrogenation at room temperature,TLC tracking, to be completely complete,Diatomaceous earth filtration,The solvent was removed by distillation under reduced pressure,To obtain a crude solid,And then beaten with ether to get pink powder,Drying to give 12.31 g of compound 7-11,Yield: 73.8percent. |
72% | With hydrogen In methanol at 20℃; | 1 equiv of 43 dissolved in methanol (anhydrous) and 10percent of 10percent Pd/C was added under a hydrogen atmosphere and allowed to stir overnight at room-temp. Reaction was filtered through a pad of celite and concentrated to give a blue/purple oil. The oil was brought up in DCM acidified using 1 M HCl and organic wash was removed. The aqueous was neutralized with sat'd sodium bicarbonate and washed 3 times with DCM, dried with sodium sulfate, filtered and concentrated and resulted in a pale red oil, 72percent yield. MS (ES) 277.8 [MH+]. |
0.457 g | With palladium 10% on activated carbon; hydrogen In methanol at 20℃; | The solvent was removed and the residue was taken up with methanol, Pd-C (10percent) was added and stirred under hydrogen overnight at room temperature and then filtered through Celite and concentrated in vacuo. The crude product was purified by flash chromatography to afford 0.457 g product (60percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With hydrogen In tetrahydrofuran | EXAMPLE 12 4-(4-Amino-phenyl)-piperazine-1-carboxylic acid tert-butyl ester To a suspension of 1.46 g (4.8 mmol) of 4-(4-nitrophenyl)-piperazine-1-carboxylic acid tert-butyl ester (Example 11) and 1 g of Raney Nickel in 50 mL of tetrahydrofuran is added hydrogen to an initial pressure of 54.5 psi. The reaction is shaken for 14 hours and then filtered. The filtrate is concentrated to give 1.29 g (97percent) of the product as a solid. MS (APCI) M+1: Calcd 278.2; Found 278.2. Anal. Calcd for C15H23N3O2: C, 64.96: H, 8.36: N, 15.15. Found: C, 65.22: H, 8.58: N, 14.58. |
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