Category: 78818-15-2

78818-15-2, Benzyl 3-oxopiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 98 1-(4-methoxyphenyl)-3-(methylsulfonyl)-6-[4-(2-oxo-1-piperazinyl)phenyl]-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one To 6-(4-iodophenyl)-1-(4-methoxyphenyl)-3-(methylsulfonyl)-1,4,5,6-tetrahydro-7H-pyrazolo(3,4-c)pyridin-7-one (0.55 g, 1.0 mmol), 4-benzyloxycarbonylpiperazin-2-one (0.35 g,1.4 mmol),and K2CO3 (0.23 g,1.6 mmol) was added DMSO (5 mL). The mixture was degassed with N2. CuI (39 mg, 0.21 mmol) was added and the reaction was heated to 130 C. for 18 h. The reaction was diluted with EtOAc and water, extracted with EtOAc, and dried (MgSO4). Purification of the intermediate by chromatography on silica gel using 5%MeOH/CH2Cl2 was followed by deprotection in refluxing TFA. Purification by HPLC and freeze-drying afforded 175 mg (27%) of a white solid; High Resolution Mass Spec (M+H)+for C24H26N6O5S 496.1650.

78818-15-2, As the paragraph descriping shows that 78818-15-2 is playing an increasingly important role.

Reference：
Patent; Pinto, Donald J.P.; Quan, Mimi L.; Orwat, Michael J.; Li, Yun-Long; Han, Wei; Qiao, Jennifer X.; Lam, Patrick Y.S.; Koch, Stephanie L.; US2003/191115; (2003); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

78818-15-2, Benzyl 3-oxopiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

78818-15-2, Step C Preparation (+-)-4-Benzyloxycarbonyl-1-[1-(3-(benzyloxy)phenyl)-3-buten-1-yl]-2-piperazinone Sodium hydride (1.20 g, 30.0 mmol, 60% mineral oil dispersion) was triturated with hexane. The flask was charged with 15 mL of dimethylformamide and cooled to 0 C. 4-Benzyloxycarbonyl-2-piperazinone was added (4.55 g, 19.4 mmol), and the reaction was stirred for 15 minutes at 0 C. A solution of the product from Step B (4.83 g, 14.5 mmol) in 15 mL of dimethylformamide was added slowly, and the reaction was allowed to warm to room temperature. After 3 days, the solution was concentrated in vacuo, and partitioned between EtOAc and saturated NaHCO3 solution. The aqueous phase was extracted with EtOAc, and the combined organics were washed with saturated NaHCO3 soln and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resulting product was purified by silica gel chromatography (10% EtOAc/hexane, then 5% MeOH/CH2Cl2) to provide the titled product as a yellow oil.

The synthetic route of 78818-15-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Merck & Co., Inc.; US6562823; (2003); B1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

78818-15-2, Benzyl 3-oxopiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

78818-15-2, Step C Preparation (+-)-4-Benzyloxycarbonyl-1-[1-(3-(benzyloxy)phenyl)-3-buten-1-yl]-2-piperazinone Sodium hydride (1.20 g, 30.0 mmol, 60% mineral oil dispersion) was triturated with hexane. The flask was charged with 15 mL of dimethylformamide and cooled to 0 C. 4-Benzyloxycarbonyl-2-piperazinone was added (4.55 g, 19.4 mmol), and the reaction was stirred for 15 minutes at 0 C. A solution of the product from Step B (4.83 g, 14.5 mmol) in 15 mL of dimethylformamide was added slowly, and the reaction was allowed to warm to room temperature. After 3 days, the solution was concentrated in vacuo, and partitioned between EtOAc and saturated NaHCO3 solution. The aqueous phase was extracted with EtOAc, and the combined organics were washed with saturated NaHCO3 soln and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resulting product was purified by silica gel chromatography (10% EtOAc/hexane, then 5% MeOH/CH2Cl2) to provide the titled product as a yellow oil.

The synthetic route of 78818-15-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Merck & Co., Inc.; US6562823; (2003); B1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

78818-15-2, Benzyl 3-oxopiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

78818-15-2, Step 1 4-Benzyloxycarbonyl-[1-(2-oxo-2-(adamant-1-yl))ethyl]piperazin-2-one To a round bottomed flask were added 4-benzyloxycarbonylpiperazin-2-one (234.26 mg, 1.0 mmol) along with N,N-dimethylforamide (5.0 ml), and sodium hydride (73.0 mg (60%), 1.0 mmol). After the evolution of hydrogen had ceased the reaction was allowed to stir for an additional 30 minutes. To this was added 1 adamantyl bromomethyl ketone (257.18 mg, 1.0 mmol). The reaction stirred at Rt. for 18hrs. The reaction was poured into water (25 ml) and extracted with ethylacetate (2*25 ml). The ethylacetate layer was washed with brine and dried (MgSO4). Solvent removal yielded 4-benzyloxycarbonyl-[1-(2-oxo-2-(adamant-1-yl)ethyl]piperazin-2-one. 400 Mhz H1 NMR (CDCl3): 1.68-1.91(m,12H), 2.06 (br s,3H), 3.32(t,2H), 3.77(t,2H), 4.20(s,2H), 4.34(s,2H), 5.16(s,2H), 7.36(m,5H). The material was used with out further purification.

As the paragraph descriping shows that 78818-15-2 is playing an increasingly important role.

Reference：
Patent; Eng, Wai-Si; Lobell, Robert B.; Lumma, William C.; Smith, Anthony M.; US2002/72081; (2002); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

78818-15-2, Benzyl 3-oxopiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

78818-15-2, A mixture of 1 ,1-dimethylethyl 4-[(4-iodophenyl)oxy]-1-piperidinecarboxylate (D1 ) (10.9 g), 4-benzyloxycarbonylpiperazin-2-one (commercially available for example from Fluorochem) (7.6 g), tripotassium phosphate (6.79 g), Lambda/./V-dimethylethylenediamine (0.29 ml) and copper (I) iodide (257 mg) in dioxane (200 ml) was heated under nitrogen to 100 0C for 24 h. The mixture was allowed to cool to room temperature and partitioned between water and EtOAc. The aqueous solution was extracted with more EtOAc and the combined organic solutions were washed with brine, dried and concentrated. The residue was dissolved in DCM and purified by chromatography on Biotage (400 g) eluting with EtOAc-cyclohexane (2:3 to 1 :1 ) to give the title compound (7.36 g) LCMS RT = 3.45 min.

As the paragraph descriping shows that 78818-15-2 is playing an increasingly important role.

Reference：
Patent; GLAXO GROUP LIMITED; WO2007/9741; (2007); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

78818-15-2, Benzyl 3-oxopiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

b) 4-Methyl-l-(4-methyl-3′-nitro-3,4,5,6-tetrahydro-2H-[l,2′]bipyridinyl-6′-yl)- piperazin-2-one; To a solution of 6′-bromo-4-methyl-3′-niuO-3,4,5,6-tetrahydro-2H- [l,2′]bipyridinyl (as prepared in the previous step) (300 mg, 1.00 mmol) in toluene (5 mL) was added 3-oxo-piprazine-l-carboxylic acid benzyl ester (351 mg, 1.50 mmol), K3PO4 EPO (424 mg, 2.00 mmol) and CuI (38 mg, 0.20 mmol) followed by N,N’- dimethylethylenediamine (20 muL, 0.18 mmol) under Ar. The resulting mixture was heated at reflux overnight. The reaction mixture was allowed to cool to room temperature and filtered through a thin pad of Celite. The filtrate was concentrated in vacuo and the residue obtained was purified by chromatography on silica (20% EtOAc: hexane) to obtain 4-(4- methyl-3 ‘ -nitro-3 ,4,5 ,6-tetrahydro-2H- [1,2’ ]bipyridyl-6 ‘ -yl)-3 -oxo-piperazine- 1 – carboxylic acid benzyl ester (258 mg, 57%). This compound (453 mg, 1.00 mmol) was dissolved in 30% HBr/HOAc (1 mL). The resulting mixture was stirred at room temperature overnight and Et2O (20 mL) was added dropwise. The resulting mixture was stirred for another hour, the precipitated hydrobromide was collected by suction filtration, washed with Et2O (3×20 mL), dried in vacuo for 1 h and used directly in next step.The above hydrobromide (48 mg, 0.10 mmol) was added to 37% aq HCHO (ca. 0.05 mL, 0.05 mmol) followed by NaBH(OAc)3 (106 mg, 0.050 mmol). The resulting mixture was stirred at room temperature for 30 min and the product was extracted with CH2Cl2 (3×10 mL). The CH2Cl2 layers were combined, dried (Na2SO4) and concentrated in vacuo. The residue obtained was purified on silica (10-50% EtOAc:hexane) to obtain the title compound (27 mg, 81%). 1H-NMR (CDCl3; 400 MHz): delta 8.21 (d, IH, J=8.9 Hz), 7.58 (d, IH, J=8.9 Hz), 3.98 (m, 2H), 3.75 (m, 2H), 3.31 (s, 2H), 2.96 (m, 2H), 2.72 (m, 2H), 2.39 (s, 3H), 1.9-1.65 (m, 3H), 1.25 (m, 2H), 0.99 (d, 3H, J=6.42 Hz).

78818-15-2, 78818-15-2 Benzyl 3-oxopiperazine-1-carboxylate 736777, apiperazines compound, is more and more widely used in various fields.

Reference：
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2006/47504; (2006); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

78818-15-2, Benzyl 3-oxopiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,78818-15-2

In a sealed tube, dissolve benzyl 3-oxopiperazine-l-carboxylate (500 mg, 2.13 mmol), A- bromo-acetophenone (425 mg, 2.13 mmol), Cs2CO3 (1.4 g, 4.26 mmol), Pd2dba3 (195 mg, 0.213 mmol) and xantphos (124 mg, 0.213 mmol) in dry dioxane (10 mL). Degas the mixture with Argon and heat at 115 0C overnight. Cool and dilute with EtOAc (25 mL). Filter the solution through Ce lite and evaporate the filtrate. Chromatograph the crude product on silica eluting with hexane/acetone (2: 1) to yield the title compound. LC-MS (M+l): 353.14

The synthetic route of 78818-15-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; NEUROGEN CORPORATION; WO2007/16496; (2007); A2;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

78818-15-2,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.78818-15-2,Benzyl 3-oxopiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

Step A Preparation of benzyl 4-(3-ethoxy-3-oxopropyl)-3-oxo-1-piperazine carboxylate Phenylmethyl 3-oxopiperazinecarboxylate (234 mg, 1.0 mmol) was dissolved in anhydrous DMF (5mL) and cooled to 0 C. To this solution was added NaH (44 mg, 1.1 mmol). The reaction mixture was stirred for 1 hour and allowed to warm to room temperature. The reaction was cooled to 0 C. and bromo ethyl propionate (0.144 ml, 1.1 mmol) was added. The reaction was stirred overnight and allowed to warm to room temperature. The reaction was poured into brine and extracted 3* with EtOAc. The organic layers were combined and the solvent evaporated. The resulting residue was purified by flash chromatography yielding 250 mg (75.0%) of the desired product. MS (ES) 335 (M+H)+

78818-15-2 Benzyl 3-oxopiperazine-1-carboxylate 736777, apiperazines compound, is more and more widely used in various fields.

Reference：
Patent; Scarborough, Robert M.; Mehrotra, Mukund; Pandey, Anjali; Smyth, Mark; US2003/55244; (2003); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.78818-15-2,Benzyl 3-oxopiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.,78818-15-2

Preparation 57; 4-{5-[4-(2-Methoxy-(1S)-methyl-ethoxy)-phenyl]-[1,3,4]oxadiazol-2-ylmethyl}-3- oxo-piperazine-1-carboxvlic acid benzyl ester; A solution of potassium carbonate (136mg, 2. 4mmol) suspended in tetrahydrofuran (3mL) was cooled to 0C. Tetrabutylammonium bromide (130mg, 0. 40mol), 4-benzyloxycarbonyl piperazin-2-one (568mg, 2. 43mmol), and the product of preparation 48 (572mg, 2. 02mmol), were added in tetrahydrofuran (3mL) and the mixture was allowed to warm to room temperature and stir for 18 hours. The solvent was then evaporated under reduced pressure and the residue was dissolved in ethyl acetate and washed with water and brine. The organic phase was dried over magnesium sulfate and concentrated in vacuo to give an oil. Purification by column chromatography on silica gel, eluting with pentane: diethyl ether 90: 10 to 20: 80, gave the title compound as a pale brown foam in 70% yield, (679mg). ‘H NMR (CDCI3, 400MHz) d : 1.40 (d, 3H), 3.40 (s, 3H), 3.50 (m, 1H), 3.55 (t, 2H), 3.60 (m, 1H), 3.80 (t, 2H), 4.15 (s, 2H), 4.64 (m, 1H), 4.90 (s, 2H), 5.15 (s, 2H), 7.00 (d, 2H), 7.40 (m, 5H), 7.95 (d, 2H). MS APCI+ m/z 481 [MH] +

78818-15-2 Benzyl 3-oxopiperazine-1-carboxylate 736777, apiperazines compound, is more and more widely used in various fields.

Reference：
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/82866; (2005); A2;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

78818-15-2, Benzyl 3-oxopiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,78818-15-2

b) 2-Bromoethyl di-tert-butyl phosphate (298mg, 0. 94MMOL) in tetrahydrofuran (1. 0ml) was added at room temperature to a stirred suspension of benzyl 3-oxopiperazine-1- carboxylate (200mg, 0. 85mmol), powdered potassium hydroxide (57mg, L. OMMOL) and tetra- n-butylammonium bromide (55mg, 0.17mmol) in THF (2. 0ml). The reaction mixture was -266- stirred for 90 minutes and then filtered through Celite and the filtrate evaporated to leave a colourless oil. The crude product was purified by silica gel chromatography eluting with a 2- 5% mixture of methanol in dichloromethane to give benzyl 4-{2-[(DI-TERT- butoxyphosphoryl) oxy] ETHYL}-3-OXOPIPERAZINE-1-CARBOXYLATE (220 mg, 55% yield) as a colourless oil: 1H-NMR (CDC13) : 7.34 (m, 5H), 5.16 (s, 2H), 4.15 (s, 2H), 4.11 (m, 2H), 3.71 (m, 2H), 3.65 (m, 2H), 3.53 (m, 2H), 1.47 (s, 18H).

The synthetic route of 78818-15-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/94410; (2004); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics