Category: 109-07-9

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

109-07-9, 2-Methylpiperazine (3.19 g) was added at 0°C to 2-(tert-butylcarbonyloxyimino)-2-phenylacetonitrile (7.87 g) in tetrahydrofuran (100 mL), and the mixture was stirred for 2 hours. The reaction solvent was removed under reduced pressure, and the residue was purified through silica gel column chromatography (chloroform – 7N ammonia/methanol), to thereby give the title compound as an oil (5.70 g, 89percent). 1H-NMR(400MHz,CDCl3)delta:1.05(3H,d,J=6.4Hz), 1.46(9H,s), 2.40 (1H,br), 2.65-2.84(3H,m), 2.90-3.00 (1H,br), 3.94(2H,br). MS(ESI)m/z:201(M+H)+.

As the paragraph descriping shows that 109-07-9 is playing an increasingly important role.

Reference：
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1621537; (2006); 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 1: Preparing gatifloxacin from compound (II) 10 g (0.0339 moles, 1 equivalent) of compound (II) is placed in a flask, 30 ml of acetonitryl (3 volumes) is added and this is heated to a temperature of 76-80 C. Once reflux has been attained, and being the temperature maintained, 3.28 g (0.0203 moles, 0.6 equivalents) of hexamethyldisilazane (HMDS) is added with a compensated adding funnel. Once addition is completed, the reaction is maintained with stirring for 1 hour at a temperature of 76-80 C. Once this period has elapsed, the reaction mixture is cooled to a temperature ranging between 0 and 15 C, and 5.78 g (0.0407 moles, 1.2 equivalents) of boron trifluoride ethyletherate is added while keeping the temperature below 15 C. Once addition is completed, the temperature is allowed to rise to 15- 25 C and it is kept under these conditions for approximately 2 hours. The pH of the mixture is then adjusted to an approximate value of 9 with triethylamine (approximately 2 ml). To the resulting suspension is added a solution of 10.19 g (0.1017 moles, 3 equivalents) of 2-methylpiperazine in 28 ml of acetonitryl, while maintaining the temperature between 15 and 25 C. The resulting amber solution is kept with stirring under these conditions for approximately 3 hours. Once the reaction has been completed, the solution is distilled at low pressure until a stirrable paste is obtained. At this point 50 ml of methanol is added, the resulting suspension is raised to a temperature of 63-67’C and is kept under these conditions for approximately 5 hours. Once the reaction has been completed, the mixture is cooled to a temperature of 25-35 C in a water bath, and then at a temperature of 0-5 C in a water/ice bath for a further 1 hour. The resulting precipitate is filtered, washed with cold methanol (2 x 10 ml) and dried at 40 C in a vacuum oven to constant weight. 10.70 g of crude gatifloxacin is obtained, having a water content of 2. 95% by weight. The yield of the process is 81. 8%. The crude product is crystallised in methanol by dissolving 20 g of crude gatifloxacin in 1 1 of methanol (50 volumes) at a temperature of 63-67 C. Once all the product has been dissolved, the solution is left to cool to a temperature of 30-40 C, and then to a temperature of 0-5 C in a water/ice bath, maintaining it under these conditions for 1 hour. The resulting suspension is filtered and the solid retained is washed with 20 ml (1 volume) of cold methanol. The solid obtained is dried at 40 C in a vacuum oven to provide 18.65 g of gatifloxacin with a water content of 2. 36% by weight. The overall yield from the compound (II) is 77. 7%, with a purity exceeding 99. 8% as determined by HPLC chromatography. The content of by-product resulting from demethylation in position 8 of the ring is lower than 0. 1% as determined by HPLC chromatography., 109-07-9

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

Reference：
Patent; QUIMICA SINTETICA, S.A.; WO2005/47260; (2005); 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.109-07-9,2-Methylpiperazine,as a common compound, the synthetic route is as follows.

[Referential Example 82]; 3-Methylpiperazine-1-carboxylic acid tert-butyl ester; [] 2-Methylpiperazine (3.19 g) was added to 2-(tert-butylcarbonyloxyimino)-2-phenylacetonitrile (7.87 g) in tetrahydrofuran (100 mL) at 0C, followed by stirring for 2 hours. The residue obtained by removal through evaporation of the reaction solvent under reduced pressure was purified through silica gel column chromatography (chloroform – 7N ammonia/methanol mixture), to thereby give the title compound as an oily product (5.70 g, 89%).1H-NMR(400MHz,CDCl3)delta: 1.05(3H,d,J=6.4Hz), 1.46(9H,s), 2.40(1H,br), 2.65-2.84(3H,m), 2.90-3.00(1H,br), 3.94(2H,br). MS(ESI)m/z: 201(M+H)+.

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; DAIICHI PHARMACEUTICAL CO., LTD.; EP1591443; (2005); 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.109-07-9,2-Methylpiperazine,as a common compound, the synthetic route is as follows.

To a stirred solution of 2- methyl piperazine (l0g, lOOmmol, leq) in ethanol (200mL) was added DIPEA (43.5mL, 250mmol, and the reaction mixture stirred for 10 min.. To this Boc anhydride (21.8mL, lOOmmol, leq) was added at 0¡ãC and the resulting reaction mixture was stirred at room temperature overnight. The progress of reaction was monitored by TLC, which indicated formation of nonpolar spot. The reaction mixture was concentrated and dissolved in DCM (200mL) then washed with water (2 x 80mL) followed by brine solution. The combined organic layer was dried over Na2SC>4 and concentrated under reduced pressure to afford crude tert-butyl (S)-3-methylpiperazine-1-carboxylate (20g, crude yield 100percent) as a yellow liquid. TLC: MeOH : DCM (0.5: 9.5); R,= 0.3., 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; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ZEPEDA-VELAZQUEZ, Carlos Armando; PODA, Gennady; ISAAC, Methvin; UEHLING, David; WILSON, Brian; JOSEPH, Babu; LIU, Yong; SUBRAMANIAN, Pandiaraju; MAMAI, Ahmed; PRAKESCH, Michael; STILLE, Julia Kathleen; (1053 pag.)WO2017/147700; (2017); 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 stirred solution of 2-METHYLPIPERAZINE (2 equivalents) in DICHLOROMETHANE AT-10 C, was added di-tert-butyl dicarbonate (1 equivalent). The mixture was stirred for 10 minutes AT-10 C and was then quenched with saturated aqueous NAHC03. The two phases were separated, and the organic layer was extracted with methylene chloride. The organic extracts were collected, dried (NA2SO4), and concentrated to give the desired tert-butyl 3-methylpiperazine-carboxylate (LC/MS M/Z 201.0 (MH +), Rt 1.67 minutes). Conversion to tert-butyl 4- [2- (4-AMINO-5-FLUORO-2-OXO (3- hydroquinolyl)) benzimidazol-6-yl]-3-methylpiperazinecarboxylate was performed according to the procedure in Example 8 (LC/MS M/Z 493.3 (MH+), Rt 2.45 minutes). Subsequent removal of the Boc group was preformed by bubbling HCI gas into a MeOH solution until saturated (LC/MS M/Z 393.2 (MH +), Rt 1.95 minutes). The free amine was subsequently reacted with paraformaldehyde (5 equivalents) in MeOH: AcOH (5: 1) and NaCNBH4 (4 equivalents) over molecular sieves at 80 C. After 10 hours, the mixture was cooled, filtered, and concentrated. The residue was dissolved in CH2CI2, washed with saturated NAHC03, and dried with NA2SO4 to give the desired 4- AMINO-3-[6-(2, 4-DIMETHYLPIPERAZINYL) BENZIMIDAZOL-2-YL]-5-FLUOROHYDROQUINOLIN- 2-one (LC/MS M/Z 407.3 (MH +), Rt 2.03 minutes). Further purification was performed via reverse phase prep. HPLC.

109-07-9, 109-07-9 2-Methylpiperazine 66057, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; CHIRON CORPORATION; WO2004/18419; (2004); 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.109-07-9,2-Methylpiperazine,as a common compound, the synthetic route is as follows.

Step 1: CbzCl (17 g, 0.1 mol) was added into a solution of compound 219-1 (30 g, 0.3 mol) and DIPEA (40 g, 0.3 mol) in DCM (200 mL) at 0C, then the mixture was stirred at room temperature for 3h and the solvent was removed, the crude product was purified by column chromatography to deliver compound 2 (11 g, yield 47%) as yellow oil. MS ESI calcd for C13H18N2O2 [M+H]+ 235, found 235., 109-07-9

109-07-9 2-Methylpiperazine 66057, apiperazines compound, is more and more widely used in various fields.

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.109-07-9,2-Methylpiperazine,as a common compound, the synthetic route is as follows.

Reference Example 7 0.65 g of 2-methylpiperazine was added to a solution of 0.48 g of 1-cyclopropyl-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid in 5 ml of N-methyl-2-pyrrolidone, followed by heating at 90 C. for 20 minutes. After distilling off the solvent under reduced pressure, the residue was added with ethanol. The resulting crystals were filtered and recrystallized from ethyl acetate-ethanol to give 231 mg of 1-cyclopropyl-6-fluoro-7-(3-methyl-1-piperazinyl)-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. m.p.: 206 C.-208 C., white powder

109-07-9, 109-07-9 2-Methylpiperazine 66057, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; Otsuka Pharmaceutical Co., Ltd.; US6333431; (2001); B1;,
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.109-07-9,2-Methylpiperazine,as a common compound, the synthetic route is as follows.

To the 1200 L reactor was added [60C] racemic 2-methylpiperazine (100 kg) from a drum. H20 (240 L) was added, and the solution was cooled to [13C.] To the 1200 L receiver was added L-tartaric acid (150 kg). [H20] (140 L) was added, and the slurry was stirred for 1 h 35 min until dissolution of the solids was complete. The L-tartaric acid solution was transferred to the 1200 L reactor over 2 h while maintaining a temperature of [10-22C] in the 1200 L reactor followed by a [H20] rinse (20 L). Ethanol (163 kg) was added to the 1200 L reactor, and the solution was cooled to [2C.] The resulting slurry was stirred for 2 h at [2C,] and filtered through a 36″Nutsche filter sending the filtrate into the 1200 L receiver. The 1200 L reactor and 36″Nutsche filter were washed with H20 (200 L), and the solids were dried to yield 214 kg of 12% ee [(171%] based on the title compound). These solids were recharged to a clean 1200 L receiver and H20 (630 L) was added to the 1200 L receiver, which was heated to [85C] until all the solids had dissolved. The solution was filtered through an in-line filter (C) into the 1200 L reactor, cooled to [5C,] and stirred for 2 h. The resulting slurry was filtered through a clean 36″Nutsche filter sending the filtrate into the 1200 L receiver. The 1200 L reactor and 36″Nutsche filter were washed with [H20] (200 L), and the solids were dried to yield 104 kg of 93% ee (83% based on the title compound). These solids were recharged to a clean 1200 L receiver and [H20] (254 L) was added to the 1200 L receiver, which was heated to [85C] until all the solids had dissolved. The solution was filtered through an in-line filter (C) into the 1200 L reactor, cooled to [5C,] and stirred for 2 h. The resulting slurry was filtered through a clean 36″Nutsche filter sending the filtrate into the 1200 L receiver. The 1200 L reactor and 36″Nutsche filter were washed with H20 (200 L), and the solids were dried to yield 92 kg of 99% ee (74% based on the title compound). [D1] does not describe the preparation of the title compound but makes reference [TO J.] Med. Chem. 1990, 33, 1645-1656 (D2). The yield of the title compound according to D2, starting from racemic 2-methylpiperazine was 35%. M. Pt. 255.0-257. [0C.] ‘H NMR (400 MHz, [D20)] : [6] 4.79 [(D20,] reference), 4.36 (2H, s), 3.73-3. 64 (4H, [M),] 3.43 [(1H,] td J = 13.7, 3.0 Hz), 3.34 [(1H,] td, J = 12.7, 3.1 Hz), 3.17 [(1H,] dd, J = 14.2 12.8 Hz), 1.41 (3H, d, J = 6.1 Hz), 0.00 (TMS, reference). [13C] NMR (100 MHz, [D20)] : [6] 178.46 (s), 73.91 (d), 49.02 (d), 49.00 [(MEOH,] reference), 45.82 (t), 40.56 (t), 40.10 (t), 15.42 (q). IR (diffuse reflectance) 3426 (s), 3011 (s), 2999 (s), 2888 (s), 2785 (s, b), 2740 (s, b), 2703 (s, b), 2649 (s, b), 2483 (s, b), 2483 (s, b), 2361 (s), 2354,2340, 2248,1638 (s), cm HRMS (FAB) [CALCD FOR C5HL2N2 +HI 101.] 1079, found [101.] 1080. [[A]] [25D] = [24] (c 1.00, water). Anal. Calcd for [C4H606.] [C5HL2N2C,] 43.20 ; H, 7.25 ; N, 11.19. Found: C, 41.25 ; H, 7.45 ; N, 10.71.

109-07-9, As the paragraph descriping shows that 109-07-9 is playing an increasingly important role.

Reference£º
Patent; BIOVITRUM AB; WO2004/829; (2003); 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.109-07-9,2-Methylpiperazine,as a common compound, the synthetic route is as follows.

A solution of 2-methyl-5-fluoroquinazoline (100 mg; 0.616 MMOL ; 1EQ), 2- methylpiperazine (310 mg; 3.083 MMOL ; 5eq) and triethylamine (0.17 mL; 1.23 MMOL ; 2 eq) in dry DMF (2.5 mL) was heated at 120C for 5 h. The yellow solution was cooled and the solvent was evaporated in vacuo. The crude material was purified on SPE cartridge (Si; 2 g) eluting with a gradient from 100% dichloromethane to 85% DICHLOROMETHANE : 1% NH40H 2M sol in methanol to afford the title compound (D15) (85 mg; yield 57%). MS; (ES) m/z: 243.3 [MH+]. CAHSN4 requires 242.32. ‘H NMR (300MHZ, CDCI3) 8 : 9.48 (s, 1H), 7.81 (t, 1H), 7.48 (d, 1H), 7.10 (d, 1H), 3.03 (m, 1H), 3.23-2. 98-2.76-2. 41 (m, 6H), 2.72 (s, 3H) 1.01 (d, 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; GLAXO GROUP LIMITED; WO2004/46124; (2004); 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 5 1-Cyclopropyl-6,8-difluoro-1,4-dihydro-5-methyl-7-[3-methyl-1-piperazinyl]-4-oxo-3-quinolinecarboxylic acid A suspension of 0.80 g (2.69 mmol) of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid, 1.08 g (10.8 mmol) of 2-methylpiperazine, and 20 ml of acetonitrile was refluxed for three hours, then cooled in an ice bath. The precipitate was filtered, washed with water and acetonitrile, and dried to give 0.76 g of the title compound, mp 187-188 C., 109-07-9

As the paragraph descriping shows that 109-07-9 is playing an increasingly important role.

Reference£º
Patent; Warner-Lambert Company; US4920120; (1990); A;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics