Tag: M.W:200-300

70261-82-4, 4-(4-Methylpiperazin-1-ylmethyl)phenylamine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,70261-82-4

To a 0 0C cooled solution of 4-nitrobenzaldehyde in DCM (40 mL) was added Na(OAc)3BH (10.526gm, 49.66 mmol) and the reacton was stirred for lOmin. To the reaction mixture was added N-methylpiperazine (9.93 g, 99.3 mmol) under nitrogen atmosphere and the reaction mixture was continued stirring at room temperature for 4h. The progress of the reaction was monitored by TLC and upon completion of the reaction, the mixture was partitioned between DCM (20 mL) and water (15 mL) and the organic layer was separated, washed with water (2 x 15 mL), dried over sodium sulphate, filtered and the solvent was removed under reduced pressure to give crude residue. Washing with ether gave l-methyl-4-(4-nitrobenzyl)piperazine (4 g). 1H NMR (CDCl3, 200MHz) delta: 8.19 (2H, d, J= 8.4Hz), 7.53 (2H5 d, J= 8.4 Hz)5 3.59 (2H, s), 2.47 (8H, bm), 2.29 (3H5 s); m/e = 236 (M+l). To a solution of l-methyl-4-(4-nitrobenzyl)piperazine (4.0 g) in methanol (100 niL) at room temperature under nitrogen atmosphere was added Raney nickel (1.6gm). The reaction mixture was stirred for 2 hr under hydrogen atmosphere. The progress of the reaction was monitored by TLC and upon completion of the reaction, the mixture was filtered under nitrogen atmosphere and the solvent was removed under reduced pressure to give 4-[(4-methylpiperazin-l-yl)methyl]aniline (3.2 g). 1H NMR (CDCl3, 200MHz) delta: 7.13 (2H, d, J= 8.4 Hz)5 6.61 (2H, d5 J= 8.4 Hz), 3.41 (2H, s), 2.45 (8H, bm), 2.27 (3H, s); m/e = 206 (M+l).To a stirred solution of 4-[(4-methylpiperazin-l-yl)methyl]aniline (3.2 g, 15.57 mmol) in acetic acid: concentrated HCl (32:32 niL) at 10 0C was added NaNO2 (1.30 g,18.78 mmol) in water (16 mL) and stirred for 10 min. Freshly prepared SnCl2^H2O (11.75 g, 51.97 mmol) in concentrated HCl (32 mL) was added at 10 0C. The temperature of the reaction mixture was allowed to rise to room temperature and maintained there for 4hr. After filtering the reaction mixture, the precipitate was washed with water and the solid obtained was dried under reduced pressure to obtain l-(4-hydrazmobenzyl)-4- methylpiperazine (3.4 g). 1HNMR (CD3OD, 200MHz) delta: 7.66 (2H, d, J= 8.4 Hz), 7.13 (2H, d, J= 8.4 Hz), 4.46 (2H, s), 3.72 (8H5 bm), 3.11 (3H5 s);To a solution of l-(4-hydrazinobenzyl)-4-methylpiperazine (3.4 g, 13.25 mmol) in ethanol (50 mL) were added piperidone. HCl (2.51 g, 18.55 mmol). The reaction temperature was raised to 90 0C and continued stirring for 2 hrs. The progress of the reaction was monitored by TLC and upon completion of the reaction the mixture was cooled to rt and HCl gas was bubbled through the reaction mixture at 0 0C. After the reaction mixture was saturated with HCl, the temperature was raised to 90 0C again and continued stirring for 2hrs. The ethanolic HCl was removed under reduced pressure and the pH of the reaction mixture was adjusted to 12.0 with 10% NaOH solution. The mixture was partitioned between 20% MeOH: DCM and water (35 mL) and the organic layer was separated, dried over Na2SO4 filtered and the solvent was removed under reduced pressure to give crude residue. Washing with ether gave 8-[(4-methylpiperazin-l-yl)methyl]-2,3,4,5- tetrahydro-lNo.-pyrido[4,3-&]indole (1 g). 1HNMR(CD3OD5 200MHz) delta: 7.31 (IH, s), 7.27 (IH, d, J= 8.6 Hz), 7.06 (IH, d, J= 8.6 Hz), 4.01 (2H5 s), 3.60 (2H, s), 3.21 (8H5 bm), 2.86 (4H5 m), 2.28 (3H, s); m/e = 285 (M+l).To a solution of 8-[(4-methylpiperazin-l-yl)methyl]-2,3,4,5-tetrahydro-li- pyrido[4,3-delta]indole(0.5 g,1.76 mmol) in DMF (15 mL) at rt was added Example 7 (0.567 g, 2.64 mmol) and K2CO3 (0.731 g, 5.28 mmol). The reaction temperature was raised to 100 0C and continued stirring for 12hr. The progress of the reaction was monitored by TLC and upon completion of the reaction DMF was removed under reduced pressure. The reaction mixture was partitioned between ethyl acetate (100 mL) and water (80 mL) and the organic layer was separated, dried over sodium sulphate, filtered and the solvent was removed under reduced pressure to give crude residue. Washing with ether gave methyl 2-{8-[(4- methylpiperazin-1 -yl)methyl]-l 53s4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl}pyrimidine-5- carboxylate (0.15 g). 1HNMR (DMSO-D6, 200MHz) delta: 8.84 (2H, s), 7.94 (lH,s), 7.67 (IH, d, J= 8.6 Hz), 7.54 (IH, d, J= 8.6 Hz), 5.01 (2H, s), 3.80-3.01 (1OH, m), 2.87 (3H, s); m/e = 421 (M+l).To a 00C solution of methyl 2-{8-[(4-methylpiperazin~l-yl)methyl]-l,3,4,5- tetrahydro-2H-pyrido[4,3-b]indol-2-yl}pyrimidine-5-carboxylate (0.1 g) in MeOH: DCM (5:2 mL) was added 50% aqueous hydroxylamine solution (2 mL) and to the mixture was added a solution of NaOH (0.08 g) in water (1 mL). The reaction mixture was stirred at room temperature for lhr and the progress of the reaction was monitored by TLC and upon completion of the reaction the solvent was removed under reduced pressure. The pH of the mixture was adjusted to 7.5 using IN HCl and the obtained solid was filtered and washed with water followed by diethyl ether. After filtering, t…

The synthetic route of 70261-82-4 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; MIKANA THERAPEUTICS, INC.; WO2006/88949; (2006); 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.262368-30-9,N-(4-Aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide,as a common compound, the synthetic route is as follows.

General procedure: To a suspension of methyl (Z)-1-acetyl-3-(ethoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate (6) (500 mg,1.368 mmol) in DMF (3.5 mL) was added N-(4-aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide (14) (395 mg,1.505 mmol, 1.1 equiv.) at RT. After heating the reaction mixture at 80 C for 1 h, it was allowed to cool to RT. Piperidine (297 lL,3.010 mmol, 2.2 equiv.) was then added and stirred for 2 h. Volatiles were removed in vacuo and water was added to the obtained residue and stirred for 15 min. The precipitate was then filtered under suction and cake was washed with water, then with minimum amount of cold methanol, and then ether. The obtained product was purified by column chromatography (neutral Al2O3,0-10% methanol in CH2Cl2) to afford 532 mg (72%) of target molecule 15., 262368-30-9

The synthetic route of 262368-30-9 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Edupuganti, Ramakrishna; Taliaferro, Juliana M.; Wang, Qiantao; Xie, Xuemei; Cho, Eun Jeong; Vidhu, Fnu; Ren, Pengyu; Anslyn, Eric V.; Bartholomeusz, Chandra; Dalby, Kevin N.; Bioorganic and Medicinal Chemistry; vol. 25; 9; (2017); p. 2609 – 2616;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

31166-44-6, 1-Cbz-Piperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 : DIPEA (879 mu, 5.17 mmol) was added to 5-bromo-2-chloropyrimidine Ex.10a (500 mg, 2.56 mmol) in acetonitrile (12 mL). Then, benzyl piperazine-1-carboxylate (500 mu, 2.56 mmol) was added to the mixture. The reaction mixture was stirred at r.t. for 60h. Water and EtOAc were added. The two phases were separated and the aqueous solution was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered and the solution was concentrated to dryness. The crude material was purified by column chromatography on silica gel eluting with Heptane/EtOAc from [100:0] to [0:100]. The product fractions were combined and concentrated to dryness to afford benzyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate Ex.10a (858 mg, 88percent) as white solid.

31166-44-6, The synthetic route of 31166-44-6 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; GENFIT; DELHOMEL, Jean-Francois; PERSPICACE, Enrico; MAJD, Zouher; PARROCHE, Peggy; WALCZAK, Robert; BONNET, Pascal; FOGHA, Jade; (76 pag.)WO2018/138356; (2018); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

187669-60-9, 1-(4-(Methylsulfonyl)phenyl)piperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 81; 4-{2-[4-(4-Mcthancsulfonylphcnyl)pipcrazin-l-yl]-2-oxocthyl}pipcridinc-l- carboxylic acid tert-butyl ester; To a solution of 4-hydroxy-4-(3-hydroxypropyl)piperidine-l-carboxylic acid tert-butyl ester (1.00 g, 3.86 mmol) in DCM (60 mL) was added Dess-Martin periodinane (1.80 g, 4.24 mmol) and the mixture was stirred for Ih at rt, a further batch of Dess-Martin periodinane (0.20 g, 0.47 mmol). The reaction mixture was quenched with 2 M NaOH and extracted with Et2O, the aqueous phase was re-extracted with Et2O and the organic extracts were combined then washed with water, 2 M NaOH solution and brine, dried (MgSO4) and the solvent was removed under vacuum to give 2-hydroxy-l-oxa-8-azaspiro[4.5]decane-8-carboxylic acid tert-butyl ester. A solution of l-(4-methanesulfonylphenyl)piperazine (0.12 g, 0.50 mmol) and 2-hydroxy-l-oxa- 8-azaspiro[4.5]decane-8-carboxylic acid tert-butyl ester (0.14 g, 0.56 mmol) in anhydrous MeOH (2 mL) was heated at 750C for Ih, then NaBH4 (25 mg, 0.65 mmol) was added and the reaction was stirred for 2h. The solvent was removed under vacuum and the resulting residue was partitioned between water and DCM. The aqueous phase was re-extracted with DCM, the EPO organic extracts were combined and purified by flash chromatography eluting with 3:97 MeOH:DCM to afford the title compound: RT = 2.37 min; m/z (ES+) = 482.45 [M+H]+., 187669-60-9

187669-60-9 1-(4-(Methylsulfonyl)phenyl)piperazine 735904, apiperazines compound, is more and more widely used in various fields.

Reference：
Patent; PROSIDION LIMITED; WO2007/3964; (2007); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

639068-43-2, tert-Butyl 3,5-dimethylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

639068-43-2, Referential Example 88]; 3,4,5-Trimethylpiperazine-1-carboxylic acid tert-butyl ester ; 3,5-Dimethylpiperazine-1-carboxylic acid tert-butyl ester (3.31 g) obtained from Referential Example 87 was dissolved in methanol (50 mL). To the resultant solution, 10percent palladium-carbon (0.504 g), 35percent aqueous formalin (1.85 mL), and 1M HCl in ethanol (15.4 mL) were added at room temperature, and the mixture was stirred in a hydrogen atmosphere for 19 hours. 10percent Palladium-carbon (0.95 g), 35percent aqueous formalin (1.8 mL), and 1M HCl-ethanol (15 mL) were added thereto, followed by stirring in a hydrogen atmosphere for 23 hours. After the system was purged with nitrogen, the resultant mixture was neutralized through addition of the aqueous sodium hydroxide, and insoluble matter was removed by filtration. The filtrate was brought to dryness under reduced pressure. The residue was purified through silica gel column chromatography (chloroform – 7N ammonia/methanol), to thereby give the title compound as an oily product (2.28 g, 65percent).1H-NMR(400MHz,CDCl3)delta: 1.08(6H,d,J=6.1Hz), 1.45(9H,s), 2.00-2.20(2H,m), 2.25(3H,s), 2.60(2H,br), 3.85(2H,br). MS(FAB)m/z: 229(M+H)+.

The synthetic route of 639068-43-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1591443; (2005); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

55121-99-8, (4-Aminophenyl)(4-methylpiperazin-1-yl)methanone is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The mixture of B (10.92g, 20.0mmol)), HATU (9.12g, 24.0mmol) and DIEA (3.87g, 30.0mmol) in DMF (lOOmL) was stirred at room temperature for 0.5h, then was added la (5.26g, 24.0mmol). The resulting mixture was stirred at room temperature for 0.5h and evaporated. The residue was purified by columnchromatography (EA:MeOH=5:l) to provide lb (12.43g, 83.2%)., 55121-99-8

55121-99-8 (4-Aminophenyl)(4-methylpiperazin-1-yl)methanone 231408, apiperazines compound, is more and more widely used in various fields.

Reference：
Patent; XCOVERY HOLDING COMPANY, LLC; LIANG, Congxin; WO2012/48259; (2012); A2;,
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.314741-40-7,(S)-tert-Butyl 3-(hydroxymethyl)piperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

Step A: (S)-tert-butyl 4-((S)-2-hydroxy-2-( 4-methyl-1-oxo-1 ,3-dihydroisobenzofuran-5-yl)ethyl)-3-(hydroxymethyl)piperazine-1-carboxylate: (S)-4-Methyl-5-( oxiran-2-yl)isobenzofuran-1 (3H)one(0.75g, 3.95 mmol) and (S)-tert-butyl3-(hydroxymethyl)piperazine-1-carboxylate (1.02 g,4.73 mmol) in ethanol (12 mL) were heated in microwave at 150 oc for 1.5 h. The reaction solution was concentrated and the residue was purified by MPLC on a Biotage system using 40-100% ethyl acetate/hexane to give the title compound. LC/MS: (M+1)+: 407.15., 314741-40-7

As the paragraph descriping shows that 314741-40-7 is playing an increasingly important role.

Reference：
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; BLIZZARD, Timothy; CHOBANIAN, Harry; DE JESUS, Reynalda; DING, Fa-Xiang; DONG, Shuzhi; GUDE, Candido; KIM, Dooseop; TANG, Haifeng; WALSH, Shawn; PIO, Barbara; JIANG, Jinlong; WO2013/28474; (2013); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

502649-29-8, 1-Boc-3-Benzylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

502649-29-8, To a solution of tert-butyl 3-benzylpiperazine-1-carboxylate (300 mg, 1.09 mmol) in DCM (10 mL) was added TEA (330 mg, 0.45 mL, 3.26 mmol) and CbzCl (278 mg, 0.23 mL, 1.63 mmol). After the reaction mixture was then stirred at rt for 2 hrs. The mixture was diluted with water, and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give crude product which was purified by column chromatography to give a product (368 mg) as an oil. The oil was dissolved in DCM (2 mL), then TFA (124 mg, 84 muL, 1.09 mmol) was added. The reaction mixture was stirred at rt overnight, then concentrated to give a crude compound 77a (385 mg) as an oil which is directly used in next step. MS: calc?d 311 (MH+), measured 311 (MH+).

As the paragraph descriping shows that 502649-29-8 is playing an increasingly important role.

Reference：
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; LIU, Haixia; SHEN, Hong; ZHU, Wei; HU, Taishan; ZHANG, Zhiwei; DEY, Fabian; (91 pag.)WO2020/52738; (2020); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

115619-01-7, 4-(4-Ethylpiperazin-1-yl)phenylamine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 59; 6-Acetyl-8-ethyl-2-[4-(4-ethylpiperazin-l-yl)phenylamino]-4-methylpyrido[2,3-c(jpyrimidin-7(8H)-one; [00246] A mixture of 6-bromo-8-ethyl-4-methyl-2-(methylsulfonyl)-6- phenylpyrido[2,3-J]pyrimidin-7(8H)-one from above (502 mg, 1.46 mmol) and 4-(4- ethylpiperazin-l-yl)aniline (3.45 g, 16.8 mmol) were heated (the neat mixture melted upon heating) at 170 C for ten minutes and cooled to room temperature. The reaction was partitioned between aqueous and organic layers with ethyl acetate and H2O. The organic layer was dried with anhydrous magnesium sulfate, filtered and evaporated, and directly applied to prep-LC to provide product (320 mg, 46.5 % yield); 471.0 [M+H]., 115619-01-7

115619-01-7 4-(4-Ethylpiperazin-1-yl)phenylamine 936738, apiperazines compound, is more and more widely used in various fields.

Reference：
Patent; EXELIXIS, INC.; WO2007/44698; (2007); 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.216144-45-5,4-(4-Methylpiperazin-1-yl)benzylamine,as a common compound, the synthetic route is as follows.

To a solution of 4- (4-methylpiperazin-1-yl) benzylamine (43 mg, 0.21 mmol) in toluene (4 mL) under nitrogen protection was added trimethylaluminum (0.2 mL, 1 M n-hexane solution), The reaction system was stirred at room temperature for 15 minutes, and 4,9-dioxo-4,9-dihydrothiazolo [5,4-g] isoquinoline-2-carboxylic acid ethyl ester (20 mg, 0.07 mmol) was added. The reaction system Stir at 90 C for 5 hours.The reaction solution was concentrated under reduced pressure andpurifiedby prep-HPLC (NH4HCO3system) to obtain compound 8 (2 mg, yield: 7%) as a yellow solid.

216144-45-5, 216144-45-5 4-(4-Methylpiperazin-1-yl)benzylamine 2776493, apiperazines compound, is more and more widely used in various fields.

Reference：
Patent; Shanghai Dinuo Pharmaceutical Technology Co., Ltd.; Zhao Zhiming; (42 pag.)CN110467629; (2019); A;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics