Heterocyclic Building Blocks-piperazine

103-76-4, N-(2-Hydroxyethyl)piperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 2-(piperazin-l-yl)ethanol (1. 3g, 0.01 mol) and (Boc)20 (2.4 g, 0.01 1 mol) in MeOH (15 mL) was added Et3N (1.52 g, 0.015 mol). The mixture was stirred at room temperature for 3 h. The solvent was removed in vacuo. The residue was diluted with water and extracted with EtOAc (3×20 mL). The combined organic layers were washed with brine then dried over MgSC^. After filtration and concentration, the product (2 g, 87 %) was obtained as an oil. 1H NMR (300 MHz, CDC13): delta 3.74 (t, 2H, J = 5.3 Hz), 3.56 (t, 4 h, J = 5.0 Hz), 2.72 (t, 2H, J = 5.1 Hz), 2.66 (t, 4 h, J = 5.0 Hz), 1.44 s, 9H). LCMS: No molecular ion observed for desired mass., 103-76-4

The synthetic route of 103-76-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HERMANN, Johannes Cornelius; KUGLSTATTER, Andreas; LUCAS, Matthew C.; PADILLA, Fernando; WANNER, Jutta; ZHANG, Xiaohu; WO2013/64445; (2013); A1;,
Piperazine – Wikipedia
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1030377-21-9, (S)-1-Boc-2-(Hydroxymethyl)piperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Into a 250-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of tert-butyl (2S)-2-(hydroxymethyl)piperazine-1-carboxylate (11.4 g, 52.7 mmol, 1.0 equiv) in DMSO (60 mL), 1,4-diiodobenzene (19.1 g, 59.9 mmol, 1.1 equiv), CuI (0.9 g, 5.2 mmol, 0.1 equiv), K2CO3 (14.5 g, 105.4mmol, 2.0 equiv), L-Proline (1.2 g, 10.4 mmol, 0.2 equiv). The resulting mixture was stirred for 12 hours at 90 C in an oil bath. The reaction was then quenched by the addition of 200 mL of water/ice. The resulting solution was extracted with ethyl acetate (200 mL x 2). The residue was applied onto a silica gel column eluting with ethyl acetate/petroleum ether (1:1). This resulted in 4.2 g (18.8%) of tert-butyl (2S)- 2-(hydroxymethyl)-4-(4-iodophenyl) piperazine-1-carboxylate as a solid. LC/MS (ESI) m/z: 419.05 [M+1] +., 1030377-21-9

The synthetic route of 1030377-21-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ARVINAS OPERATIONS, INC.; YALE UNIVERSITY; CREW, Andrew P.; HORNBERGER, Keith R.; WANG, Jing; CREWS, Craig M.; JAIME-FIGUEROA, Saul; DONG, Hanqing; QIAN, Yimin; ZIMMERMAN, Kurt; (1451 pag.)WO2020/51564; (2020); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

67455-41-8, 4-(Piperazin-1-yl)aniline is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

67455-41-8, A mixture of 4-(piperazin-l-yl)aniline (348 mg, 1.968 mmol), (E)-methyl 3-(2-(2-chloropyrimidin-5-yl)vinyl)-5-methoxybenzoate (600 mg, 1.968 mmol) and TFA (672 mg, 5.904 mmol) in propan-2-ol (30 mL) was stirred at 150 C for 40 min under microwave. The resulting mixture was concentrated, basified with ammonia water, purified via ISCO (DCM/MeOH) to afford the title compound as a yellow solid (320 mg, 36.6% yield). MS (m/z): 446.3(M+H)+.

The synthetic route of 67455-41-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; ZHANG, Weihan; LI, Jinshui; WO2014/139145; (2014); A1;,
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21655-48-1, cis-2,6-Dimethylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1: Compound 250-2 (1.14 g, 10 mmol) was added into a solution of compound 250-1 (1.71 g, 10 mmol) and K2CO3 (2.78 g, 20 mmol) in DMF (20 mL), the reaction mixture was stirred at 110¡ãC for 2h, monitored by LCMS till completion. Then the mixture was poured into H2O, extracted with EtOAc, the organic phase was dried over anhydrous sodium sulfate, concentrated to give a crude product. The crude product was purified by silica gel column chromatography (PE:EtOAc=1:1) to deliver compound 250-3 (2.3 g, yield 92percent) as oil. MS ESI calcd for C13H19N3O2[M+H]+ 250, found 250., 21655-48-1

As the paragraph descriping shows that 21655-48-1 is playing an increasingly important role.

Reference£º
Patent; GUANGDONG ZHONGSHENG PHARMACEUTICAL CO., LTD; WU, Hao; LIN, Jun; LI, Yunhui; WEI, Changqing; CHEN, Shuhui; LONG, Chaofeng; CHEN, Xiaoxin; LIU, Zhuowei; CHEN, Lijuan; (212 pag.)EP3124482; (2017); 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.13754-38-6,1-Benzoylpiperazine,as a common compound, the synthetic route is as follows.

To a solution of 4-(3-(4-cyanophenyl)imidazo[l,2-a]pyridin-6-yl)benzoic acid (100 mg, 0.294 mmol) in DMF (1.5 mL) were added HATU (168 mg, 0.441 mmol), N-methyl morpholine (129 iL, 1.18 mmol) and 1-benzoylpiperazine (67 mg, 0.441 mmol). The reaction mixture was stirred at room temperature under inert atmosphere for 18 h then, was diluted with water (15 mL) and extracted with EtOAc (3×30 mL). The combined organic layer was dried over Na2S04 and was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, eluent CHCl3/MeOH 92:8) to afford 4-(6-(4- (4-benzoylpiperazine- 1 -carbonyl)phenyl)imidazo[ 1 ,2-a]pyridin-3 -yl)benzonitrile (75 mg, 50%, AUC HPLC 99%) as a white solid. NMR (400 MHz, DMSO- 6) delta 8.75 (s, 1H), 7.95-7.89 (m, 4H), 7.88 (s, 1H), 7.82-7.55 (m, 4H), 7.59 (d, J= 8.0 Hz, 2H), 7.63-7.43 (m, 5H), 4.00-3.40 (m, 8H); 13C NMR (100 MHz, CD3OD): delta 172.90, 172.34, 147.49, 140.29, 136.50, 136.11, 134.87, 134.76, 134.43, 131.43, 129.87, 129.48, 129.22, 128.63, 128.59, 128.21, 127.85, 126.61, 122.92, 119.55, 118.51, 112.76; MS (ESI) m/z 512 [C32H25N50 + H]+..

13754-38-6, 13754-38-6 1-Benzoylpiperazine 762654, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; NACRO, Kassoum; DURAISWAMY, Athisayamani, Jeyaraj; CHENNAMANENI, Lohitha, Rao; WO2013/147711; (2013); A1;,
Piperazine – Wikipedia
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5294-61-1,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5294-61-1,N-(2,6-Dimethylphenyl)-2-(piperazin-1-yl)acetamide,as a common compound, the synthetic route is as follows.

A mixture OF N- (2, 6-dimethylphenyl) -2-piperazinylacetamide (100 mg, 0.4 mmol) and 1- (2-methoxyphenyl) but-3-en-2-one (100 mg, 0.56 mmol), a compound of formula (12), in ethanol (2 mL) was heated at reflux for 16 hours. Ethanol was removed under reduced pressure and the residue was purified by preparative TLC, using 10% methanol in dichloromethane as mobile phase, to afford N (2, 6-dimethylphenyl)-2- {4- [4- (2-methoxyphenyl)-3-oxobutyl] piperazin-1- yl} acetamide, a compound of formula (13).

The synthetic route of 5294-61-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; CV THERAPEUTICS, INC.; WO2004/63180; (2004); 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.115761-79-0,1-(2,4-Difluorophenyl)piperazine,as a common compound, the synthetic route is as follows.

A mixture of the 2- (5-amino-2- (furan-2-yl) -8H-pyrazolo [4, 3-e] [1, 2, 4] triazolo [1, 5-c] pyrimidin-8-yl) -4-methylpentanoic acid (35.5 mg, 0.1 mmol) , 1- (2, 4-difluorophenyl) piperazine (19.8 mg, 0.1 mmol) , HATU (46 mg, 0.12 mmol) and DIPEA (25.8 mg, 0.2 mmol) in DMF (3 mL) was stirred overnight. The reaction mixture was poured into H2O (15 mL) and extracted with EtOAc (20 mL x 3) . The combined organic layers were washed with brine, dried over Na2SO4, concentrated and purified by column chromatography (petroleum ether/EtOAc = 10: 1 3: 1) to give the target compound (20 mg, 37.3%) .1H NMR (400 MHz, DMSO-d6) delta 8.78 (s, 1H) , 7.94 (s, 1H) , 7.65 (s, 2H) , 7.25 -7.17 (m, 2H) , 7.03 (m, 2H) , 6.74 (dd, J = 3.2, 1.6 Hz, 1H) , 5.69 (m, 1H) , 3.76 (s, 2H) , 3.64 (m, 2H) , 3.05-2.93 (m, 2H) , 2.91 -2.79 (m, 2H) , 2.28 -2.17 (m, 1H) , 1.89 -1.78 (m, 1H) , 1.35 (m, 1H) , 0.97 (d, J = 6.4 Hz, 3H) , 0.88 (d, J = 6.4 Hz, 3H) ppm. MS: M/e 536 (M+1)+., 115761-79-0

The synthetic route of 115761-79-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BEIGENE, LTD.; ZHANG, Guoliang; SUN, Hanzi; ZHOU, Changyou; (253 pag.)WO2020/20097; (2020); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

109-07-9, 2-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 2 A reaction was performed as described for Example 1, except that the amount of benzyl chlorocarbonate used was changed from 8.45 g to 9.25 g (= 0.0533 mole, 1.07 molar times). As a result, the reaction yield of 1-benzyloxycarbonyl-3-methylpiperazine was 91.7% (based on the amount of 2-methylpiperazine) after lapse of 2 hours at 0 to 5C. Furthermore, the reaction solution was stirred at room temperature for further 12 hours and analyzed. As a result, the reaction yield was 94.5%. From the obtained reaction solution, 1-butanol was distilled away, and 30 g of water was added to the concentrate. The pH was adjusted to 11.2 using 48% sodium hydroxide. To the solution, 40 g of toluene was added, and the lower layer was removed. Subsequently, the upper layer was concentrated under reduced pressure to distill away toluene, for obtaining 11.1 g of a recovered solution. The obtained recovered solution was analyzed, and as a result, the intended 1-bunzyloxycarbonyl-3-methylpiperazine occupied 87.2 area %, and as for impurities, benzyl alcohol occupied 0.52 area %, 1-benzyl-4-benzyloxycarbonyl-2-methylpiperazine, 0.01 area %, 1-benzyl-2-methylpiperazine, 0.10 area %, and 1,4-dibenzyloxycarbonyl-2-methylpiperazine, 11.9 area % (solvent toluene, 1.9 area %). Therefore, the total of impurities was 6 liquid chromatography area %. Example 12 The reaction solution obtained by the same operation as in Example 2 was concentrated and 31 g of 1-butanol was distilled away under reduced pressure, being followed by addition of 30 g of water. Subsequently 35% hydrochloric acid water was used for adjusting the pH to 0.8. Then, 22 g of toluene was added, and stirring was carried out for 30 minutes. The upper layer was then removed, and the same amount of toluene was added again. The same operation was repeated for carrying out washing operation. Subsequently 48% sodium hydroxide aqueous solution was used to keep the pH of the reaction solution at 11.5. In this case, white turbidity occurred due to liberated 1-benzyloxycarbonyl-3-methylpiperazine. To the white turbid solution, 40 g of toluene was added, and stirring was carried out for 30 minutes. The lower layer was then removed, and the upper layer was concentrated under reduced pressure at 60 to 70C in temperature. Then, toluene was distilled away to obtain 10.13 g of 1-benzyloxycarbonyl-3-methylpiperazine. The obtained compound was analyzed. As a result, the intended 1-benzyloxycarbonyl-3-methylpiperazine accounted for 98.0 liquid chromatography area %. The impurities showed 0.40 liquid chromatography area % for benzyl alcohol, 0.04 liquid chromatography area % for 1-benzyl-4-benzyloxycarbonyl-2-methylpiperazine, 0.10 liquid chromatography area % for 1-benzyl-2-methylpiperazine and no detection for 1,4-dibenzyloxycarbonyl-2-methylpiperazine (1.46 liquid chromatography area % for solvent toluene). Therefore, the total of impurities was 0.55 liquid chromatography area %.Example 13 The reaction solution obtained by the same operation as in Example 2 was concentrated and 28 g of 1-butanol was distilled away under reduced pressure, being followed by addition of 30 g of water. Subsequently 35% hydrochloric acid water was used for adjusting the pH to 0.7. Then, 22 g of toluene was added, and stirring was carried out for 30 minutes. The upper layer was then removed, and the same amount of toluene was added again. The same operation was repeated for carrying out washing operation. Subsequently 48% sodium hydroxide aqueous solution was used to keep the pH of the reaction solution at 11.8. In this case, white turbidity occurred due to liberated 1-benzyloxycarbonyl-3-methylpiperazine. To the white turbid solution, 40 g of toluene was added, and stirring was carried out for 30 minutes. The lower layer was then removed, and the upper layer was concentrated under reduced pressure at 60 to 70C in temperature. Then, toluene was distilled away. Ten point three two grams of the obtained 1-benzyloxycarbonyl-3-methylpiperazine was placed in a 10 ml heart flask and distilled in vacuum. When the oil bath reached 145C, the removal by distillation started, and the temperature was raised finally up to 170C. The internal pressure ranged from 40 to 53 Pa, and the temperature at the column top ranged from 131 to 140C. The obtained compound was analyzed. As a result, the intended 1-benzyloxycarbonyl-3-methylpiperazine accounted for 99.7 liquid chromatography area %. The impurities showed 0.03 liquid chromatography area % for benzyl alcohol, 0.18 liquid chromatography area % for 1-benzyl-4-benzyloxycarbonyl-2-methylpiperazine, 0.04 liquid chromatography area % for 1-benzyl-2-methylpiperazine and no detection for 1,4-dibenzyloxycarbonyl-2-methylpiperazine (for solvent toluene either). Therefore, the total of impurities was 0.25 liquid chromatography area %.

109-07-9, The synthetic route of 109-07-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Toray Fine Chemicals Co., Ltd.; EP1548010; (2005); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

13754-38-6, 1-Benzoylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 4-(3-(4-cyanophenyl)imidazo[1,2-a]pyridin-6-yl)benzoic acid (100 mg, 0.294 mmol) in DMF (1.5 mL) were added HATU (168 mg, 0.441 mmol), N-methyl morpholine (129 muL, 1.18 mmol) and 1-benzoylpiperazine (67 mg, 0.441 mmol). The reaction mixture was stirred at room temperature under inert atmosphere for 18 h then, was diluted with water (15 mL) and extracted with EtOAc (3*30 mL). The combined organic layer was dried over Na2SO4 and was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, eluent CHCl3/MeOH 92:8) to afford 4-(6-(4-(4-benzoylpiperazine-1-carbonyl)phenyl)imidazo[1,2-a]pyridin-3-yl)benzonitrile (75 mg, 50%, AUC HPLC 99%) as a white solid. 1H NMR (400 MHz, DMSO-d6) delta 8.75 (s, 1H), 7.95-7.89 (m, 4H), 7.88 (s, 1H), 7.82-7.55 (m, 4H), 7.59 (d, J=8.0 Hz, 2H), 7.63-7.43 (m, 5H), 4.00-3.40 (m, 8H); 13C NMR (100 MHz, CD3OD): delta 172.90, 172.34, 147.49, 140.29, 136.50, 136.11, 134.87, 134.76, 134.43, 131.43, 129.87, 129.48, 129.22, 128.63, 128.59, 128.21, 127.85, 126.61, 122.92, 119.55, 118.51, 112.76; MS (ESI) m/z 512 [C32H25N5O+H]+.

13754-38-6, As the paragraph descriping shows that 13754-38-6 is playing an increasingly important role.

Reference£º
Patent; Agency for Science, Technology and Research; Nacro, Kassoum; Duraiswamy, Athisayamani Jeyaraj; Rao, Lohitha; US2014/371199; (2014); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

109-07-9, 2-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirring solution of 2-methylpiperazine 7 (3 g, 30.00 mmol) in CH2C12 (100 mL) under argon atmosphere were added triethylamine (9 mL, 90.00 mmol) and Boc-anhydride (7.2 mL, 33.00 mmol) at 0 C; warmed to RT and stirred for 16 h. The reaction was monitored by TLC; after completion of the reaction, the volatiles were removed in vacuo. The crude was washed with -pentane (2 x 20 mL) and dried in vacuo to afford compound 9 (5 g, 83%) as off- white solid. TLC: 5% MeOH/ CH2C12 (R/. 0.4); 1H-NMR (OMSO-d6, 400 MHz): delta 3.80- 3.62 (m, 2H), 3.27-3.09 (m, 2H), 2.83-2.71 (m, 2H), 2.37-2.17 (m, 1H), 1.39 (s, 9H), 0.92 (d, J= 6.3 Hz, 3H)., 109-07-9

The synthetic route of 109-07-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION; ARNOLD, Lee Daniel; MAAG, Hans; TURNER, JR., William W.; (274 pag.)WO2016/168619; (2016); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics