Category: 304897-49-2

304897-49-2, tert-Butyl 4-(4-aminobenzyl)piperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[0328] A mixture of intermediate 31 (0.10 g, 0.35 mmol), 4-(4-amino-benzyl)-piperazine- 1-carboxylic acid tert-butyl ester (0.12 g, 0.41 mmol), Pd2(dba)3 (30 mg, 0.033 mmol), Xantphos (35 mg, 0.06 mmol) and cesium carbonate (0.23 g, 0.71 mmol) in dioxane/DMF (3/1, 4 mL) was sealed in a microwave reaction tube and irradiated with microwave at 160 0C for 20 min. After cooling to room temperature, the cap was removed and the resulting mixture filtered. The filtered solid was washed with DCM and the filtrate concentrated. The residue was purified by flash chromatography on silica gel (hexanes to 60% EtOAc/hexanes) to afford the Boc-protected precursor. To a solution of the precursor in DCM (5 mL) was added TFA (3 mL). The mixture was stirred at room temperature for 1 h, concentrated and the residue purified by HPLC. The corrected fractions were combined and poured into saturated NaHCO3 solution (30 mL). The combined aqueous layers were extracted with EtOAc (2 x 30 mL) and the combined organic layers washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and then taken up in minimum amount of EtOAc. Hexanes were added until solid precipitated. After filtration, the title compound was obtained as a white solid (13 mg, 9%).[0329] 1H NMR (500 MHz, DMSO-d6): delta 2.11 (s, 3H), 2.30-2.40 (m, 4H), 2.83 (t, J= 4.8 Hz5 4H), 3.37 (s, 2H), 3.75 (s, 3H), 7.08 (d, J= 8.6 Hz, 2H), 7.29 (d, J= 8.6 Hz, IH), 7.43 (dd, J= 8.6, 2.2 Hz, IH), 7.47 (d, J= 2.2 Hz, IH), 7.59 (d, J= 8.6 Hz, 2H), 7.91 (s, IH), 8.37 (s, IH), 8.99 (s, IH). MS (ES+): m/z 439 (M+H)+.

304897-49-2, As the paragraph descriping shows that 304897-49-2 is playing an increasingly important role.

Reference：
Patent; TARGEGEN, INC.; WO2007/53452; (2007); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

304897-49-2, tert-Butyl 4-(4-aminobenzyl)piperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

d: Ethyl 4-(4-((4-(tert-butoxycarbonyl)piperazin- 1 -yl)methyl)phenylamino)-2-chloro- 6-methylpyrimidine-5-carboxylate Ethyl 2,4-dichloro-6-methylpyrimidine-5-carboxylate (0.5 g, 2.1 mmol) and tert-butyl 4-(4-aminobenzyl)piperazine-l-carboxylate (0.6 g, 2.06 mmol) were dissolved in NMP and stirred at 0C for 2 hour. The reaction mixture was poured onto water and extracted with EtOAc. The organic layer was washed with water, dried over a2S04 and evaporated under vacuum to get the desired compound (0.62 g). XH NMR (400 MHz, CDC13): delta 10.58 (s, 1H), 7.58 (d, J = 6.4 Hz, 2H), 7.31 (d, J = 6.4 Hz, 2H), 4.45 (q, J = 6.8 Hz, 2H), 3.56 (s, 2H), 3.41 (m, 4H), 2.69 (s, 3H), 2.47 (m, 4H), 1.45 (s, 9H), 1.43 (t, J = 6.8 Hz, 3H); MS m/z 490.0 (M+l).

304897-49-2, As the paragraph descriping shows that 304897-49-2 is playing an increasingly important role.

Reference：
Patent; ENDO PHARMACEUTICALS INC.; VENKATESAN, Aranapakam; SMITH, Roger, Astbury; HOSAHALLI, Subramanya; POTLURI, Vijay; PANIGRAHI, Sunil, Kumar; BASETTI, Vishnu; KUNTU, Karunasree; WO2013/28818; (2013); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

304897-49-2, tert-Butyl 4-(4-aminobenzyl)piperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

d: Ethyl 4-(4-((4-(tert-butoxycarbonyl)piperazin- 1 -yl)methyl)phenylamino)-2-chloro- 6-methylpyrimidine-5-carboxylate Ethyl 2,4-dichloro-6-methylpyrimidine-5-carboxylate (0.5 g, 2.1 mmol) and tert-butyl 4-(4-aminobenzyl)piperazine-l-carboxylate (0.6 g, 2.06 mmol) were dissolved in NMP and stirred at 0C for 2 hour. The reaction mixture was poured onto water and extracted with EtOAc. The organic layer was washed with water, dried over a2S04 and evaporated under vacuum to get the desired compound (0.62 g). XH NMR (400 MHz, CDC13): delta 10.58 (s, 1H), 7.58 (d, J = 6.4 Hz, 2H), 7.31 (d, J = 6.4 Hz, 2H), 4.45 (q, J = 6.8 Hz, 2H), 3.56 (s, 2H), 3.41 (m, 4H), 2.69 (s, 3H), 2.47 (m, 4H), 1.45 (s, 9H), 1.43 (t, J = 6.8 Hz, 3H); MS m/z 490.0 (M+l).

304897-49-2, As the paragraph descriping shows that 304897-49-2 is playing an increasingly important role.

Reference：
Patent; ENDO PHARMACEUTICALS INC.; VENKATESAN, Aranapakam; SMITH, Roger, Astbury; HOSAHALLI, Subramanya; POTLURI, Vijay; PANIGRAHI, Sunil, Kumar; BASETTI, Vishnu; KUNTU, Karunasree; WO2013/28818; (2013); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

304897-49-2, tert-Butyl 4-(4-aminobenzyl)piperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

d: Ethyl 4-(4-((4-(tert-butoxycarbonyl)piperazin- 1 -yl)methyl)phenylamino)-2-chloro- 6-methylpyrimidine-5-carboxylate Ethyl 2,4-dichloro-6-methylpyrimidine-5-carboxylate (0.5 g, 2.1 mmol) and tert-butyl 4-(4-aminobenzyl)piperazine-l-carboxylate (0.6 g, 2.06 mmol) were dissolved in NMP and stirred at 0C for 2 hour. The reaction mixture was poured onto water and extracted with EtOAc. The organic layer was washed with water, dried over a2S04 and evaporated under vacuum to get the desired compound (0.62 g). XH NMR (400 MHz, CDC13): delta 10.58 (s, 1H), 7.58 (d, J = 6.4 Hz, 2H), 7.31 (d, J = 6.4 Hz, 2H), 4.45 (q, J = 6.8 Hz, 2H), 3.56 (s, 2H), 3.41 (m, 4H), 2.69 (s, 3H), 2.47 (m, 4H), 1.45 (s, 9H), 1.43 (t, J = 6.8 Hz, 3H); MS m/z 490.0 (M+l).

304897-49-2, As the paragraph descriping shows that 304897-49-2 is playing an increasingly important role.

Reference：
Patent; ENDO PHARMACEUTICALS INC.; VENKATESAN, Aranapakam; SMITH, Roger, Astbury; HOSAHALLI, Subramanya; POTLURI, Vijay; PANIGRAHI, Sunil, Kumar; BASETTI, Vishnu; KUNTU, Karunasree; WO2013/28818; (2013); 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.304897-49-2,tert-Butyl 4-(4-aminobenzyl)piperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

Step 1. Preparation of tert-Butyl 4-(4-(4-bromobenzamido)benzyl)piperazine-1-carboxylate (3) 4-Bromobenzoic acid (1, 685.0 mg, 3.4 mmol) and HATU (1298.1 mg, 3.4 mmol) are partially dissolved in DMF (10 mL) at rt. DIEA (560 muL, 3.4 mmol) is added to this mixture to give a pale yellow solution. After stirring at rt for 30 min, tert-butyl 4-(4-aminobenzyl)piperazine-1-carboxylate (2, 992.9 mg, 3.4 mmol) is added and the resulting reaction mixture is heated at 60 C. for 20 h, allowed to cool to rt, and poured into water (100 mL). This mixture is extracted with Et2O (3*150 mL). The combined organic extracts are evaporated to dryness to give a white solid, which is washed with water (50 mL) and dried in vacuo. This material is used in the next synthetic step without further purification. HPLC: tR 1.67 min (method 1). LC-MS m/z calcd for C23H2879BrN3O3 ([M]+), 473. found, 474 ([M+H]+). 1H NMR (CD3OD): delta 1.46 (s, 9H), 2.96 (m, 4H), 3.59 (m, 4H), 4.05 (br s, 2H), 7.46 (m, 2H), 7.69 (m, 2H), 7.78 (m, 2H), 7.85 (m, 2H).

304897-49-2, The synthetic route of 304897-49-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ACHILLION PHARMACEUTICALS, INC.; Wiles, Jason Allan; Gadhachanda, Venkat; Chen, Dawei; Wang, Qiuping; Hashimoto, Akihiro; Pais, Godwin; Wang, Xiangzhu; Deshpande, Milind; Phadke, Avinash; US9125904; (2015); B1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

304897-49-2, tert-Butyl 4-(4-aminobenzyl)piperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4-(4-Carboxy-phenyl)-thiazole-2-carboxylic acid, (100 mg, 0.4 mmol) was combined with HATU (304 mg, 0.8 mmol). This mixture was dissolved in 3 mL of DMF and DIEA (1.0 mmol, 0.17 mL) was added to the solution. Reaction mixture was stirred at room temperature for 30 minutes. To this was added 4-(4-amino-benzyl)-piperazine-l- carboxylic acid tert-butyl ester (233.1 mg, 0.8 mmol). Reaction mixture was heated at 6O0C overnight. The crude was purified using reverse phase HPLC to give the desired product.

304897-49-2, 304897-49-2 tert-Butyl 4-(4-aminobenzyl)piperazine-1-carboxylate 12045001, apiperazines compound, is more and more widely used in various fields.

Reference：
Patent; GENELABS TECHNOLOGIES, INC.; WO2008/154601; (2008); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

304897-49-2, tert-Butyl 4-(4-aminobenzyl)piperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

d: Ethyl 4-(4-((4-(tert-butoxycarbonyl)piperazin- 1 -yl)methyl)phenylamino)-2-chloro- 6-methylpyrimidine-5-carboxylate Ethyl 2,4-dichloro-6-methylpyrimidine-5-carboxylate (0.5 g, 2.1 mmol) and tert-butyl 4-(4-aminobenzyl)piperazine-l-carboxylate (0.6 g, 2.06 mmol) were dissolved in NMP and stirred at 0C for 2 hour. The reaction mixture was poured onto water and extracted with EtOAc. The organic layer was washed with water, dried over a2S04 and evaporated under vacuum to get the desired compound (0.62 g). XH NMR (400 MHz, CDC13): delta 10.58 (s, 1H), 7.58 (d, J = 6.4 Hz, 2H), 7.31 (d, J = 6.4 Hz, 2H), 4.45 (q, J = 6.8 Hz, 2H), 3.56 (s, 2H), 3.41 (m, 4H), 2.69 (s, 3H), 2.47 (m, 4H), 1.45 (s, 9H), 1.43 (t, J = 6.8 Hz, 3H); MS m/z 490.0 (M+l).

304897-49-2, As the paragraph descriping shows that 304897-49-2 is playing an increasingly important role.

Reference：
Patent; ENDO PHARMACEUTICALS INC.; VENKATESAN, Aranapakam; SMITH, Roger, Astbury; HOSAHALLI, Subramanya; POTLURI, Vijay; PANIGRAHI, Sunil, Kumar; BASETTI, Vishnu; KUNTU, Karunasree; WO2013/28818; (2013); 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.304897-49-2,tert-Butyl 4-(4-aminobenzyl)piperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

In a round bottomed flask under nitrogen atmosphere commercially available benzoic acid (1.1 mmol) or sulphonyl chloride was suspended in 75 ml of anhydrous DCM. Then HOBt (1.4 mmol) and EDO HCI (1.1 mmol) were added and the resulting mixture stirred at room temperature for 2 hours. Then a solution of intermediates (X) (compounds of examples 4-6 of Table 2) (1.1 mmol) in 75 ml of dry DCM was addedand the mixture stirred at 40 00 upon completion. The reaction mixture was left to cool to room temperature, washed with a saturated aqueous solution of NH4CI, then aqueous HCI 0.5M, aqueous NaOH 1 M and finally with a saturated aqueous solution of NaHCO3. The organic layer was separated, dried over sodium sulphate, filtered and evaporated under vacuum. The resulting crude product was purified by flashchromatography on silica gel, eluting with a gradient from cyclohexane/AcOEt 1/1 to100% AcOEt. The collected fractions were evaporated to give the compounds of examples 7-10,14., 304897-49-2

As the paragraph descriping shows that 304897-49-2 is playing an increasingly important role.

Reference：
Patent; ROTTAPHARM BIOTECH S.R.L.; ARTUSI, Roberto; CASELLI, Gianfranco; ROVATI, Lucio; (78 pag.)WO2016/146220; (2016); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

304897-49-2, tert-Butyl 4-(4-aminobenzyl)piperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[0328] A mixture of intermediate 31 (0.10 g, 0.35 mmol), 4-(4-amino-benzyl)-piperazine- 1-carboxylic acid tert-butyl ester (0.12 g, 0.41 mmol), Pd2(dba)3 (30 mg, 0.033 mmol), Xantphos (35 mg, 0.06 mmol) and cesium carbonate (0.23 g, 0.71 mmol) in dioxane/DMF (3/1, 4 mL) was sealed in a microwave reaction tube and irradiated with microwave at 160 0C for 20 min. After cooling to room temperature, the cap was removed and the resulting mixture filtered. The filtered solid was washed with DCM and the filtrate concentrated. The residue was purified by flash chromatography on silica gel (hexanes to 60% EtOAc/hexanes) to afford the Boc-protected precursor. To a solution of the precursor in DCM (5 mL) was added TFA (3 mL). The mixture was stirred at room temperature for 1 h, concentrated and the residue purified by HPLC. The corrected fractions were combined and poured into saturated NaHCO3 solution (30 mL). The combined aqueous layers were extracted with EtOAc (2 x 30 mL) and the combined organic layers washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and then taken up in minimum amount of EtOAc. Hexanes were added until solid precipitated. After filtration, the title compound was obtained as a white solid (13 mg, 9%).[0329] 1H NMR (500 MHz, DMSO-d6): delta 2.11 (s, 3H), 2.30-2.40 (m, 4H), 2.83 (t, J= 4.8 Hz5 4H), 3.37 (s, 2H), 3.75 (s, 3H), 7.08 (d, J= 8.6 Hz, 2H), 7.29 (d, J= 8.6 Hz, IH), 7.43 (dd, J= 8.6, 2.2 Hz, IH), 7.47 (d, J= 2.2 Hz, IH), 7.59 (d, J= 8.6 Hz, 2H), 7.91 (s, IH), 8.37 (s, IH), 8.99 (s, IH). MS (ES+): m/z 439 (M+H)+.

304897-49-2, As the paragraph descriping shows that 304897-49-2 is playing an increasingly important role.

Reference£º
Patent; TARGEGEN, INC.; WO2007/53452; (2007); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

304897-49-2, tert-Butyl 4-(4-aminobenzyl)piperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Compound 10 A mixture intermiediate 1 (100 mg, 0.33 mmol), tert-butyl 4-(4-aminobenzyl)piperazine-l- carboxylate (96 mg, 0.33 mmol),, and DIPEA (0.15 ml, 0.82 mmol) in DMSO (5 ml) was stirred at room temperature for 30 min. After checking the TLC, the mixture was added to water (100ml). After cooled with ice-bath, the solids were collected by filtration, washed by water. After air-drying at room temperature overnight, the solids were suspended into DCM/MeOH (10/1, 5 mL) and 1 ml of TFA was added. The mixture was stirred at room temperature for overnight. After concentrated, the residue was dissolved into DCM/MeOH (8/2, 15 ml) and sat. Sodium bicarbonate solution was added to pH about 7. The organic was dried over sodium sulfate and concentrated. The crude product was purified by column chromatography (silica gel, 0-15% MeOH in DCM) to give the desired product as light yellow solids (15 mg, 10% yield). 1H MR (400 MHz, DMSO-d6) delta 11.48 (br, 1H), 10.06 (s, 1H), 8.90 (m, 2H), 8.28 (m, 1H), 7.48 (m, 2H), 7.29 (m, 2H), 7.13 (m, 1H), 6.94 (m, 1H), 6.23 (s, 1H), 3.53 (m, 2H), 3.09 (m, 4H), 2.54 (m, 4H), 2.40 (m, 3H); ESI-MS: calcd for C25H24FN70 457, found 458 (MH+). HPLC: retention time: 13.75 min. purity: 91%.

304897-49-2, 304897-49-2 tert-Butyl 4-(4-aminobenzyl)piperazine-1-carboxylate 12045001, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; NANTBIOSCIENCE, INC.; TAO, Chunlin; POLAT,, Tulay; WEINGARTEN, Paul; NALLAN, Laxman; ARP, Forrest; WANG, Qinwei; HO, David; (129 pag.)WO2016/138527; (2016); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics