Category: 74879-18-8

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, General procedure: To a stirred solution of 39 (5.0 g, 13.5 mmol) in DMF (42 mL) were added triethylamine (3.8 mL) and 1-(pyridin-3-ylmethyl)-piperazine (3.2 g, 18.1 mmol) at room temperature under nitrogen. The stirred mixture was heated at 50C for 3 h. The reaction mixture was cooled to room temperature and diluted with water, THF and EtOAc. The organic extract was washed with water, dried over Na2SO4, filtrated and then concentrated. The crude solid was washed with Et2O/EtOAc and filtrated to afford the title compound 40 as a white solid (6.33 g, 12.4 mmol, 91.5%).

The synthetic route of 74879-18-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Nagao, Satoshi; Yamane, Yoshinobu; Funasaka, Setsuo; Tanaka, Keigo; Miyazaki, Kazuki; Kotake, Yoshihiko; Kamata, Jun-Ichi; Watanabe-Miyano, Saori; Toyama, Osamu; Ozawa, Yoichi; Mizui, Yoshiharu; Okamoto, Kiyoshi; Ito, Daisuke; Bioorganic and Medicinal Chemistry; vol. 22; 19; (2014); p. 5513 – 5529;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

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

C. Preparation of (S)-5-bromo-4-(3-methylpiperazin-1-yl)-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine. To a mixture of pyrrolopyrimidine from step B (76 mg, 0.2 mmol) and (S)-2-methylpiperazine (21 mg, 0.2 mmol) in isopropanol (2 ml) was added triethylamine (0.11 ml, 0.8 mmol). The mixture was heated at 80 C. for 5 mins via microwave and concentrated under vacuum to give crude (S)-5-bromo-4-(3-methylpiperazin-1-yl)-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (65 mg, 0.15 mmol, 75%) which was used directly for the next step. MS (ES+) [M+H]+=437., 74879-18-8

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

Reference£º
Patent; Harrison, Bryce Alden; Kimball, Spencer David; Mabon, Ross; Rawlins, David Brent; Rice, Dennis S.; Voronkov, Michael Victor; Zhang, Yulian; US2009/42893; (2009); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

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, To (S)-2-methyl piperazine (0.150 g, 1.5 mmol) was added 4-bromobenzotrifluoride (0.225g, 1.0 mmol), dichloro-bis(tri-o-tolyphosphine) palladium (II) (0.236 g, 0.3mmol), and sodium t-butoxide (0.144 g, 1.5 mmol), and toluene (2 mL) sequentially. After nitrogen was bubbled through the mixture for 15 minutes, the reaction was heated to lOO’C. The reaction was stirred at 1000C for 2 hr. The reaction was filtered through celite and concentrated under reduced pressure. The residue was then purified on a 1000 micron preparative thin layer chromatography plate eluting with 5% MeOH in dichloromethane to yield the title compound as an oil. IH NMR (500 MHz, CDCl3) delta 7.5 (d, 2H, J=8.7Hz), 6.95 (d, 2H, J = 8.7 Hz), 3.71 (d, 2H, J=IOHz), 3.20 (m, IH), 3.04 (m, 2H), 2.85 (m, 1H),2.48 (m, IH), 1.24 (d, 3H, J=7.2Hz). LC/MS 247 (M+l); HPLC 2.41 min

As the paragraph descriping shows that 74879-18-8 is playing an increasingly important role.

Reference£º
Patent; MERCK & CO., INC.; WO2007/70173; (2007); A2;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

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;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics