Month: October 2020

74879-18-8, (S)-(+)-2-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

74879-18-8, Example 14 A 1-liter four-neck flask with a thermometer, condenser and stirrer was charged with 100.2 g (= 1.00 mole) of 2-methylpiperazine provided as a racemic modification, 90.0 g (= 0.600 mole) of D-tartaric acid, 170 g of water and 48.0 g (= 0.800 mole) of acetic acid, and the temperature was raised up to 72C, being followed by aging at the temperature for 2 hours. The amount of the solvent based on the amount of 2-methylpiperazine provided as a racemic modification was 1.70 times by weight. Then, cooling was carried out down to 15C, taking 12 hours, and precipitated crystals were collected by filtration. The obtained crystals were dried in vacuum, to obtain 112.4 g (= 0.449 mole) of a diastereomer salt. The optical purity of the salt was 94.4%ee, and the yield of the S-isomer in the obtained salt based on the amount of the S-isomer in the 2-methylpiperazine provided as a racemic modification was 87.3%. Then, a 500 ml flask was charged with 190 g of water, and 112.4 g of the obtained crystals {pure (S)-2-methylpiperazine content = 43.7 g} were added. Perfect dissolution was achieved at 80 to 85C, and cooling was carried out down to 15C, taking 12 hours. Precipitated crystals were collected by filtration and dried in vacuum to obtain 99.1 g of a salt. Its optical purity was 99.4%ee, and the yield of the S-isomer in the obtained salt based on the amount of (S)-2-methylpiperazine in the supplied crystals was 90.5%. A 1-liter four-neck flask with a thermometer, condenser and stirrer was charged with 300 g of water, and 98.3 g of the previously obtained salt of (S)-2-methylpiperazine and D-tartaric acid {pure (S)-2-methylpiperazine content = 39.2 g = 0.391 mole, optical purity of 2-methylpiperazine = 99.4%ee} and 39.6 g (= 0.508 mole) of 95% pure calcium hydroxide were added into the flask. The slurry was stirred in a range from 80 to 82C for 3 hours, and cooled to room temperature. Then, the non-dissolved salt (calcium tartarate) was filtered away, to obtain the mother liquor. The mother liquor was GC-analyzed, and as a result, it was found that 39.1 g (= 0.390 mole) of optically active 2-methylpiperazine existed in the mother liquor (yield 99.8%). Furthermore, as a result of HPLC analysis, the optical purity of (S)-2-methylpiperazine was 99.4%ee. Then, concentration was carried out to a water content of about 50 wt%, and 1-butanol was added, and azeotropic dehydration was carried out till the water content of the system became less than 1 wt%. In a 100 ml four-neck flask, 5.0 g of the obtained (S)-2-methylpiperazine (= 0.0499 mole, optical purity 99.4%ee) was placed, and 44 g of 1-butanol was added for dissolution. The solution was cooled down to 0C, and 9.25 g (= 0.0534 mole) of benzyl chlorocarbonate was added dropwise with the liquid temperature kept in a range from 0 to 8C. Then, stirring was carried out at 0C for 2 hours, and 30 g of 1-butanol was distilled away under reduced pressure. Subsequently 30 g of water was added, and 35% hydrochloric acid water was used to adjust the pH to 1.0. Then, 22 g of toluene was added, and stirring was carried out for 30 minutes. Subsequently the upper layer was removed, and the same amount of toluene was added again. The same operated was repeated to carry out washing operation. Then, 48% sodium hydroxide aqueous solution was used to adjust the pH of the reaction solution to 11.8. In this case, white turbidity occurred due to the 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, toluene being then distilled away. Ten point three two grams of the obtainedl-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 area %. The impurities showed 0.03 area % for benzyl alcohol, 0.12 for 1-benzyl-4-benzyloxycarbonyl-2-methylpiperazine, 0.08 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 0.23 wt%. Furthermore, the optical purity was 99.4%ee.

74879-18-8 (S)-(+)-2-Methylpiperazine 2734219, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; Toray Fine Chemicals Co., Ltd.; EP1548010; (2005); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1188265-73-7,tert-Butyl 3-(2-hydroxyethyl)piperazine-1-carboxylate,as a common compound, the synthetic route is as follows.,1188265-73-7

Step 2: 3-(2-Hydroxy-ethyl)-piperazine-1-carboxylic acid tert-butyl ester (58 mg, 0.25 mmol) was dissolved in 4 mL of dichloromethane and 1 mL of DIPEA, and then triphosgene (27 mg, 0.09 mmol) was added at room temperature. The reaction mixture was stirred for 30 minutes, and the solvent was removed in vacuo. The residue was dissolved in 3 mL of dichloromethane and 1 mL of TFA. After the reaction mixture was stirred for 1 hour, the solvent was removed in vacuo to give hexahydro-pyrazino[1,2-c][1,3]oxazin-6-one trifluoro acetitic acid salt (Compound D) as a crude product which was used directly without further purification. LC/MS: calc’d 157 (MH+), exp 157 (MH+).

As the paragraph descriping shows that 1188265-73-7 is playing an increasingly important role.

Reference£º
Patent; HOFFMANN-LA ROCHE INC.; Guo, Lei; Hu, Taishan; Kou, Buyu; Lin, Xianfeng; Shen, Hong; Shi, Houguang; Yan, Shixiang; Zhang, Weixing; Zhang, Zhisen; Zhou, Mingwei; Zhu, Wei; US2015/252057; (2015); A1;,
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76003-29-7, 1-Boc-3-Oxopiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of tert-butyl 3-oxopiperazine-1-carboxylate (5.00 g, 25.0 mmol) in DMF (50 mL) at 0 C. was added NaH (60% in mineral oil, 1.20 g, 30.0 mmol). The mixture was stirred for 30 min, and then methyl 2-bromoacetate (2.60 mL, 27.5 mmol) was added. The reaction was stirred at room temperate for 16 hours, then quenched with H2O (50 mL) and extracted with EtOAc (50 mL¡Á3). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column (pet ether:EtOAc 5:1 to 2:1) to afford the desired compound as a colorless oil (4.0 g). Yield 59% (86% purity, UV=214 nm, ESI 217.0 (M+H)+)., 76003-29-7

As the paragraph descriping shows that 76003-29-7 is playing an increasingly important role.

Reference£º
Patent; Lazuli, Inc.; Harrison, Bryce A.; Bursavich, Matthew G.; Brewer, Mark; Gerasyuto, Aleksey I.; Hahn, Kristopher N.; Konze, Kyle D.; Lin, Fu-Yang; Lippa, Blaise S.; Lugovskoy, Alexey A.; Rogers, Bruce N.; Svensson, Mats A.; Troast, Dawn M.; (172 pag.)US2018/244648; (2018); A1;,
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Piperazines – an overview | ScienceDirect Topics

889958-14-9, 1-Boc-2-oxopiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

889958-14-9, EXAMPLE 35 t-Butyl 3-Oxo-2-(alpha-hydroxy-4-fluorobenzyl)-1-piperazine carboxylate (35) To a solution of diisopropylamine (3.1 ml, 22 mmole) and dry THF (5 ml) at 0 C. under argon is added dropwise a hexane solution of n-butyllithium (13.8 ml, 22 mmole). After 3/4 hour, a solution of 2 (2.0 g, 10 mmole) in 75 ml of dry THF is added dropwise and stirred at 0 C. for 3 hours and 4-fluoro-benzaldehyde (13.6 g, 11 mmole) added dropwise. The reaction mixture was stirred at room temperature for 68 hours, poured into water, and extracted into ether. The extract was washed with brine, dried over MgSO4, and concentrated under reduced pressure, and the residue recrystallized from ethanol to give 35. M.p. 219 C. (dec.)

889958-14-9 1-Boc-2-oxopiperazine 21868412, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; Richardson-Merrell Inc.; US4341698; (1982); A;,
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Piperazines – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.169447-70-5,(S)-tert-Butyl 2-methylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

169447-70-5, To a stirred solution of tert-butyl (2S)-2-methylpiperazine-1-carboxylate(1 g, 4.99 mmol, 1 equiv.) and DIEA(1.3 g, 9.99 mmol, 2 equiv.) in DMA(10 mL) was added 4,5-dibromo-2,3- dihydropyridazin-3-one (1.5 g, 5.91 mmol, 1.183 equiv.) in portions at 100 degrees C overnight. The reaction liquid was purified by reverse phase flash with the following conditions: (0292) MeCN/H2O (NH4CO3: 5%) (MeCN: 50%-95%,40 min) to afford tert-butyl (2S)-4-(5-bromo-6- oxo-1,6-dihydropyridazin-4-yl)-2-methylpiperazine-1-carboxylate(1.2g,64.39%) as a yellow solid.

The synthetic route of 169447-70-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.314741-39-4,(S)-1-tert-Butyl 3-methyl piperazine-1,3-dicarboxylate,as a common compound, the synthetic route is as follows.

314741-39-4, A solution of 3-iodopicolinic acid 2a (1.8 g, 7.23 mmol), (S)-l-tert-butyl 3-methyl piperazine-1,3- dicarboxylate (1.766 g, 7.23 mmol), HATU (3.02 g, 7.95 mmol), DIEA (5.05 mL, 28.9 mmol) in DCM (100 mL) / Acetonitrile (20 mL) was stirred at r.t. for 12 h. DCM (50 mL) and satd. H4Cl (100 mL) were added. The DCM layer was washed with brine, dried over Na2S04, filtered and concentrated. The reaction was purified by column chromatography and the product was eluted by EtOAc to yield (S)-l-tert-butyl 3-methyl 4-(3-iodopicolinoyl)piperazine-l,3-dicarboxylate 2b.

314741-39-4 (S)-1-tert-Butyl 3-methyl piperazine-1,3-dicarboxylate 1501855, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; RAO, Ashwin, U.; MCKITTRICK, Brian Alexander; LOMBARDO, Matthew; HICKS, Jacqueline, D.; MCCRACKEN, Amy Bittner; CHU, Hong Dong; SO, Sung-Sau; ORTH, Peter; WU, Zhicai; LAN, Ping; DEBENHAM, John, S.; WHITEHEAD, Brent, R.; TAYLOR, Jerry, A.; SUN, Zhongxiang; KATIPALLY, Revathi Reddy; GABLE, Jonathan, E.; DAHLGREN, Markus, K.; BHAT, Sathesh, P.; (104 pag.)WO2018/93695; (2018); A1;,
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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.

Add to the reaction flask(E) -4 – [(2-methoxybenzylidene)Benzyl acetate-2-yl]3-nitrobenzoate (III) (4.47 g, 10 mmol),N- (4-aminophenyl) -N-methyl-2- (4-methylpiperazin-1-yl)Acetamide (IV)(2.88 g, 11 mmol) and 50 mL of dioxane, the temperature was raised to 80-85 C and the reaction was stirred for 2.5 hours.Cooled to room temperature, acid-added acid lithium carbonate (1.1 g) was added, and the mixture was stirred at room temperature for 3 hours.The reaction solution was poured into 150 mL of water to precipitate a solid.The crude product was recrystallized from methanol to give a pale yellow solid (Z) -4 – {[2- (N-methyl-2- (4-methylpiperazin-1-yl)Acetamidanilide) benzylidene]Benzyl acetate-2-yl}3-nitrobenzoate(V) 4.93 g, yield 73.9%.

262368-30-9, As the paragraph descriping shows that 262368-30-9 is playing an increasingly important role.

Reference£º
Patent; Suzhou Mirac Pharma Technology Co.,Ltd; Xu, Xuenong; (7 pag.)CN104262232; (2016); B;,
Piperazine – Wikipedia
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.132710-90-8,1-Boc-4-(3-hydroxypropyl)piperazine,as a common compound, the synthetic route is as follows.

To 0.5 g (2.05 mmol) of tert-butyl 4-(3-hydroxypropyl)piperazine-1-carboxylate, 0.3 g (2.46 mmol) of 4-hydroxybenzaldehyde and 1 g (3.07 mmol) of resin-supported triphenyl-phosphine (3 mmol/g of resin) diluted in 14.5 ml of anhydrous tetrahydrofuran, is added dropwise at 0C under argon 0.614 ml (3.07 mmol) of diisopropyldiazene-1,2-dicarboxylate. The reaction mixture is stirred at room temperature for 20h. The solid is filtered then rinsed in dichloromethane. The filtrate is concentrated and diluted in a sodium hydroxide solution (1M) and the product is extracted several times with ethyl acetate. The organic phases are combined, dried over magnesium sulfate, and concentrated. The residue is purified by chromatography on silica (cyclohexane/ethyl acetate eluent: 4:6 to 100% ethyl acetate) to yield 0.58 g of tert-butyl 4-(3-(4-formylphenoxy)propyl)piperazine-l-carboxylate in the form of a colourless oil.LCMS (ESI, m/z): (M+l) 348.91H-NMR: deltaEta pm 400 MHz, DMSO: 9.87 (1H, s, CHO), 7.86 (2H, d, CH^), 7.12 (2H, d, CHaro , 4.13 (2H, t, CH2), 3.28-3.31 (4H, m, 2CH2), 2.44 (2H, t, CH2),2.31-2.34 (4H, m, 2CH2), 1.91 (2H, q, CH2), 1.40 (9H, s, 3CH3).

132710-90-8, As the paragraph descriping shows that 132710-90-8 is playing an increasingly important role.

Reference£º
Patent; PIERRE FABRE MEDICAMENT; BEDJEGUELAL, Karim; RABOT, Remi; KALOUN, El Bachir; MAYER, Patrice; MARCHAND, Arnaud; RAHIER, Nicolas; SCHAMBEL, Philippe; BIENAYME, Hugues; WO2011/45344; (2011); A1;,
Piperazine – Wikipedia
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5317-33-9, 3-(4-Methylpiperazin-1-yl)propan-1-ol is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-ethoxy-7-fluoro-3- quinolinecarbonitrile (200 mg, 0.49 mmol), 3- (4-methyl-piperazin-1-yl) propanol (155 mg, 0.98 mmol) (WO 20047212) and sodium hydride (196 mg, 4.6 mmol) in 5 mL of N, N-dimethylformamide was heated at 125C for 3 hours. The reaction mixture was poured into saturated sodium bicarbonate and stirred for 1 hour. The aqueous solution was extracted with 10% methanol in dichloromethane. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by preparative thin layer chromatography, eluting with 15% methanol in dichloromethane. Trituation with hexane provided 116 mg of 4-[(2, 4- dichloro-5-methoxyphenyl) amino]-6-ethoxy-7- [3- (4-methylpiperazin-1- yl) propoxy] quinoline-3-carbonitrile as a light brown solid, mp 137-138C. MS 542.0 (M-H) – Analysis for C27H31CI2N503-0. 6 H20 Calcd : C, 58.40 ; H, 5.84 ; N, 12. 61. Found: C, 58.31 ; H, 5.71 ; N, 12.43., 5317-33-9

As the paragraph descriping shows that 5317-33-9 is playing an increasingly important role.

Reference£º
Patent; WYETH; WO2005/47259; (2005); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

162046-66-4, 4-(4-(tert-Butoxycarbonyl)piperazin-1-yl)benzoic acid is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a suspension of carboxylic acid 17b (3.5 g, 11.4 mmol) in THF (15 mL)containing a drop of DMF was added 1?1?-carbonyldiimidazole (1.24 g, 13.7mmol) in a single portion. The mixture was left to stir at room temperature for 18hours. A stock solution of free-base guanidine was prepared as follows:Guanidine HCl (3.22 g, 34.2 mmol) was added to an aqueous NaOH solution (2M, 10 mL). The THF solution of the acyl imidazole was then added to the freebaseguanidine solution (10 mL) and stirred for 2 hours after which TLC indicatedcomplete consumption of the acyl imidazole and a more polar spot was observedon TLC. Spot stayed on the TLC baseline when using a solvent system of 10%MeOH in DCM but move to an RF ~of 0.4 when a few drop of 7 N NH3 in MeOHwas added to the TLC solvent. The mixture was concentrated in vacuo resulting in the formation of a pale yellowresidue which was dissolved in EtOAc (35 mL). The organic layer was washedwith water (3 x 25 mL), brine (1 x 30 mL), dried (Na2SO4), filtered, andconcentrated under vacuo to give a pale yellow syrup. The crude product wasfurther purified by flash column chromatography (silica gel, Silica Flash-Silicycle) using an eluent of dichloromethane, 5% MeOH in dichloromethane, and10% MeOH in dichloromethane to give an off-white syrup which was converted tothe hydrochloride salt using 1.25 M HCl in methanol. The methanolic solutionwas concentrated under vacuo to give 16 as a light yellow solid (540 mg, 11%)., 162046-66-4

As the paragraph descriping shows that 162046-66-4 is playing an increasingly important role.

Reference£º
Article; Jalily, Pouria H.; Eldstrom, Jodene; Miller, Scott C.; Kwan, Daniel C.; Tai, Sheldon S.-H.; Chou, Doug; Niikura, Masahiro; Tietjen, Ian; Fedida, David; Molecular Pharmacology; vol. 90; 2; (2016); p. 80 – 95;,
Piperazine – Wikipedia
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