Category: piperazines

54699-92-2, 4-Methyl-1-piperazineacetic acid is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

54699-92-2, Example 13; General Method for the Preparation of Active Esters of N-Substituted Piperazine Acetic Acid from Trifluoroacetate Esters; A solution of the trifluoroacetate in THF (0.58 M, 1.2 equiv) was added to a solid sample of N-methyl piperazine acetic acid and mixed in a vortex or shaker until a homogeneous solution was obtained. The reaction of the carboxylic acid with the trifluoroacetate ester was generally complete within 30 min for all cases except N-hydroypyrrolidinone (NHP, 18 h). The progress of conversion to the active ester was monitored by ES-MS. The amount of product and any starting material (N-MPA) could be determined by direct infusion of a sample of the reaction (in ethanol) into the ES-MS. In some cases the active ester product was precipitated as dihydrochloride salt by the addition of a solution by addition of HCl solution in dioxane (4 M, 50% volume of the reaction) followed by washing with THF, ethyl acetate and hexanes. In other cases the product was isolated from the reaction as the mono TFA salt. Addition of TFA could be performed if the bis-TFA salt was desired. Dhbt ester, Calculated MH+ = 304.14 Found = 304.20 NHP ester, Calculated MH+ = 242.15 Found = 242.20 4-NP ester, Calculated MH+ = 280.13 Found = 280.20 1H NMR (400 MHz, CDCl3) d 8.20 (d, 2H, J=9.2 Hz, aromatic protons), 7.25 (d, 2H, J=9.2 Hz, aromatic protons), 3.69-3.40 (broad, 2H, ring protons), 3.57 (s, 2H, -CH2-CO-), 3.15-2.90 (broad, 6H, ring protons), 2.78 (s, 3H, -CH3). Pfp ester, Calculated MH+ = 325.10 Found = 325.10 Pcp ester, Calculated MH+ = 404.95 Found = 405.90 3-NP ester, Calculated MH+ = 280.13 Found = 280.20 NHS ester, Calculated MH+ = 256.13 Found = 256.10

The synthetic route of 54699-92-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Applera Corporation.; US2005/148771; (2005); A1;; ; Patent; Applera Corporation.; US2005/148774; (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.954388-33-1,(R)-1-((Benzyloxy)carbonyl)-4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid,as a common compound, the synthetic route is as follows.

954388-33-1, (a) [2S]-1-Benzyloxycarbonyl-4-t-butoxycarbonyl-2-methoxycarbonylmethylpiperazine A solution of [2R]-1-benzyloxycarbonyl-4-t-butoxycarbonylpiperazine-2-carboxylic acid (prepared as in Example 1(b) and 2(a)) (4.7 g) in ethyl acetate (70 ml) containing N-methylmorpholine (1.76 ml) at 0 C. was treated with isobutyl chloroformate (2.37 ml) for 3 hours and the solution was filtered and added to an excess of diazomethane and left at room temperature for 18 hours. It was evaporated to dryness to afford the diazoketone, which was_ dissolved in dry methanol (120 ml) and treated with silver benzoate (1.99 g) in triethylamine (19.9 ml), with cooling in ice. The solution was stirred in the dark at room temperature for 18 hours, evaporated to dryness, dissolved in ethyl acetate, washed with sodium bicarbonate solution and dried over sodium sulfate. It was chromatographed on silica gel, eluding with ethyl acetate-hexane to afford an oil (3.15 g) (94% ee by chiral HPLC).

As the paragraph descriping shows that 954388-33-1 is playing an increasingly important role.

Reference£º
Patent; SmithKline Beecham Corporation and SmithKline Beecham p.l.c.; US2003/203917; (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.142-64-3,Piperazine Dihydrochloride,as a common compound, the synthetic route is as follows.

5.1.5 Preparation of 1-(2-fluorobenzoyl)piperazine (5) A solution of 2-fluorobenzoic acid (7.00 g, 0.05 mol) and CDI (8.90 g, 0.055 mol) was stirred in dry THF (30 mL) at room temperature for 30 min. In a separate round bottom flask add piperazine (10.76 g, 125 mmol) and piperazine dihydrochloride (20.0 g, 125 mmol) in 60 mL of water. Stir the reaction mixture for 5 min and add 14.0 g of NaCl. Add this brine solution to the round bottom flask containing acyl imidazole. Stir the reaction mixture for 5 hour. The mixture was filtered and the filtrate distilled by rotary evaporation to remove THF. The aqueous layer was washed with ethyl acetate (3 * 10 mL) to remove diacylated product. The PH of the aqueous layer was adjusted to about 9 using saturated solution of NaOH and washed with ethyl acetate (4 * 30 mL). The aqueous layer was discarded. The organic layer was washed with water (4 * 25 mL), dried over anhydrous Na2SO4 and concentrated by rotary evaporation and purified by flash chromatography to afford 1-(2-fluorobenzoyl)piperazine as colourless solid (4.90 g, 48%). The other intermediates 1-(2-chlorobenzoyl)piperazine (6) and 1-[3-(trifluoromethyl)benzoyl]piperazine (7) were prepared by using the general procedure described above.

142-64-3, As the paragraph descriping shows that 142-64-3 is playing an increasingly important role.

Reference£º
Article; Dong, Jinyun; Lu, Wen; Pan, Xiaoyan; Su, Ping; Shi, Yaling; Wang, Jinfeng; Zhang, Jie; Bioorganic and Medicinal Chemistry; vol. 22; 24; (2014); p. 6876 – 6884;,
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.196811-66-2,tert-Butyl 4-carbamothioylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

To a stirred solution of tert-butyl 4-carbamothioylpiperazine-1-carboxylate (synthesized according to Example 5, Step 1, 1.31 g, 5.36 mmol) in isopropanol (15 mL), tert-butyl 3-bromo-2,4-dioxopiperidine-1-carboxylate obtained in the first step (1.3 g, 4.46 mmol) was added at rt. The reaction mixture was stirred overnight at 90 C. It was cooled down to rt and evaporated under reduced pressure. Water (10 mL) was added and the desired product was extracted with diethyl ether (2 x 30 mL), dried over Na2SO4 and concentrated, affording the title product. Yield: 74% (1.42 g, yellow solid). LCMS: (Method A) 239.0 (M- Boc+H), Rt. 0.70 min, 48.39% (Max)., 196811-66-2

As the paragraph descriping shows that 196811-66-2 is playing an increasingly important role.

Reference£º
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut Gajendra; (247 pag.)WO2017/144639; (2017); A1;,
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6531-38-0, 2,2′-(Piperazine-1,4-diyl)diethanamine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6531-38-0, Example 35 (compound No.14*); l,4-bis{2-[4-fluorobenzyl)amino]ethyl}piperazine; To a solution of l,4-bis(2-aminoethyl)piperazine (0.43 g, 2.5 mmol) and 4- fluorobenzaldehyde (0.59 mL, 5.5 mmol) in absolute ethanol (20 mL), 3 A molecular sieves are added. After stirring the mixture at room temperature for 5h, NaBH4 (0.47 g,12.5 mmol) was added portionwise and the mixture was stirred for 12h at room temperature. The reaction was quentched by dropwise addition of water (20 mL) and ethanol was removed under reduced pressure. The aqueous residue was extracted with CH2Cl2 (3 x 30 mL). Combined organic layers were extracted with HCl IM. The combined aqueous layers were neutralized with NaOH IM and extracted with CH2Cl2. Combined organic layers were dried over MgSO4. Crude compound is purified by thick-layer chromatography (CH2Cl2/MeOH : 80/20).

The synthetic route of 6531-38-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM); UNIVERSITE DU DROIT ET DE LA SANTE – LILLE II; WO2006/51489; (2006); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.192130-34-0,tert-Butyl 4-(2-aminoethyl)piperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

To a mixture of 6j (0.812 g, 1.86 mmol, 1.0 equiv) in n-BuOH (30 mL) was added tert-butyl-4-(2-aminoethyl)piperazine-1-carboxylate (2.80 g, 13.0 mmol, 7.0 equiv). After heating at 100¡ã C. for 24 hrs, the solvent was removed in vacuo. The resulting residue was purified by silica gel chromatography (5percent MeOH:CH2C12) to afford carbamate 8c. MS (MH+) 630.1; Calculated 629.3 for C38H39N5O4.

192130-34-0, 192130-34-0 tert-Butyl 4-(2-aminoethyl)piperazine-1-carboxylate 1514400, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; Nunes, Joseph J.; Martin, Matthew W.; White, Ryan; McGowan, David; Bemis, Jean E.; Kayser, Frank; Fu, Jiasheng; Liu, Jinqian; Jiao, Xian Yun; US2006/46977; (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.278788-66-2,(R)-tert-Butyl 3-(hydroxymethyl)piperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

DIPEA (10.41 mL, 59.63 mmol) was added to 4,7-dichloro-6-iodo-3-nitroquinoline (10 g, 27.1 mmol) and tert-butyl (3R)-3-(hydroxymethyl)piperazine-1-carboxylate (10.55 g, 48.79 mmol) in IPA (200 mL). The resulting mixture was stirred at 80 C. for 4 h. The solvent was removed in vacuo. The crude product was purified by flash silica chromatography (0 to 80% EtOAc in petroleum ether) to afford tert-butyl (3R)-4-(7-chloro-6-iodo-3-nitroquinolin-4-yl)-3-(hydroxymethyl)piperazine-1-carboxylate (6.2 g, 42%) as a yellow solid; m/z: ES+ [M+H]+=549.

278788-66-2, As the paragraph descriping shows that 278788-66-2 is playing an increasingly important role.

Reference£º
Patent; ASTRAZENECA AB; Kettle, Jason Grant; Bagal, Sharanjeet; Robb, Graeme Richard; Smith, James Michael; Goldberg, Frederick Woolf; Cassar, Doyle Joseph; Feron, James Lyman; US2019/177338; (2019); 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.25057-77-6,1,2-Dimethylpiperazine,as a common compound, the synthetic route is as follows.

1,2-Dimethyl-piperazine (0.914 g, 8.00 mmol) and ethyl 4-fluorobenzoate (0.587 mL, 4 mmol) were dissolved in DMA (6 mL) and sealed into a microwave tube. The reaction was heated to 150 C. for 90 mins in the microwave reactor and cooled to room temperature. The reaction mixture was evaporated and the crude product was purified by silica column chromatography, eluting with 5% MeOH in DCM (containing 0.1% 0.880 ammonia). Pure fractions were evaporated to dryness to afford ethyl 4-(3,4-dimethylpiperazin-1-yl)benzoate (0.380 g, 36.2%) as a colourless waxy solid. 1H NMR (399.9 MHz, CDCl3) delta 1.15 (3H, d), 1.37 (3H, t), 2.20-2.25 (1H, m), 2.34 (3H, s), 2.37-2.41 (1H, m), 2.61-2.67 (1H, m), 2.87-2.92 (1H, m), 2.99-3.06 (1H, m), 3.58-3.62 (1H, m), 3.65-3.70 (1H, m), 4.33 (2H, q), 6.83-6.87 (2H, m), 7.90-7.94 (2H, m). MS: m/z=263 (MH+).; Ethyl 4-(3,4-dimethylpiperazin-1-yl)benzoate used as starting material was prepared as follows:1,2-Dimethylpiperazine (2.284 g, 20.00 mmol) and ethyl 4-fluorobenzoate (1.467 mL, 10 mmol) were dissolved in DMA (12 mL) and sealed in a microwave tube. The reaction was heated to 150 C. for 90 mins in the microwave reactor and cooled to room temperature. The reaction mixture was heated for a further 30 mins at 150 C. and cooled to room temperature. The reaction mixture was evaporated and the crude product was purified by silica column chromatography, eluting with 5% MeOH in DCM with 0.1% 0.880 ammonia. Pure fractions were evaporated to dryness to afford ethyl 4-(3,4-dimethylpiperazin-1-yl)benzoate (0.853 g, 32.5%) as a colourless waxy solid. 1H NMR (399.9 MHz, CDCl3) delta 1.14 (3H, d), 1.37 (3H, t), 2.20-2.25 (1H, m), 2.33 (3H, s), 2.34-2.41 (1H, m), 2.62 (1H, t), 2.87-2.91 (1H, m), 2.99-3.05 (1H, m), 3.57-3.62 (1H, m), 3.65-3.70 (1H, m), 4.33 (2H, q), 6.83-6.87 (2H, m), 7.90-7.94 (2H, m). MS: m/z 263., 25057-77-6

25057-77-6 1,2-Dimethylpiperazine 198037, apiperazines compound, is more and more widely used in various.

Reference£º
Patent; ASTRAZENECA AB; US2008/153812; (2008); A1;,
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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

Thermometer, vacuum stirrer, four-necked flask 2L equipped with acooling tube, L- tartaric acid 270g (1.8 mol), acetic acid 108 g (1.8 mol), water 270g was added,was completely dissolved. Then, (¡À) -2- methylpiperazine 300g (3.0 mol), water 300g wasadded, and the reaction was heated 85 C or more, were completely dissolved. Then cooled to6874 C, (R) -2- methylpiperazine and L- diastereomers tartaric was added to precipitatecrystals, allowed to 1 hour aged at that temperature. Then, over a period of 5 hours and cooled to1218 C, and the precipitated crystals were filtered, diastereomeric salt 440g of wet biomass,liquid content 22.7wt%, optical purity of 92.3% e. e. , R KaradaOsamuritsu Retrieving salt to theR-isomer of charge (¡À) in the 2-methyl piperazine, was 88%. Then, charged 644g of water four-necked flask 2L, the resulting crystals 440g ((R) -2-methylpiperazine pure content = 132 g) were added. Furthermore, the addition of calciumhydroxide 162g (2.2mol), then heated to 80 C, and aged at that temperature for 5 hours.Cooled over a period of 2 hours up to 25 C, was filtered off precipitated crystals to remove thewet material crystal of 586g (mainly L- tartaric acid calcium). Get the filtrate 660 g, liberated with L- tartaric acid in the filtrate (R) -2- methylpiperazine were present 130 g. Thermometer, vacuum stirrer, four-necked flask 1L with a cooling tube equippedfiltrate 330g obtained in Reference Example 1 (in the filtrate of (R)-2-methyl-piperazine 65 g)was concentrated under reduced pressure, (R ) concentration of 2-methyl piperazine was distilledoff the water until the 30 percent. Then, toluene 356g was added to the concentrate, a mixedsolution was heated under normal pressure and azeotroped with water and toluene in arms 84 to87 C, excluding the water. Then, toluene was distilled off 212g under reduced pressure. Theconcentrate was cooled to 47 C, (R) -2- methylpiperazine 0.01g was added as a seed crystal toprecipitate crystals, followed by aging for 1 hour at 47 C. Was cooled over 5 hours 05 C,and aged for 2 hours at 06 C. The precipitated crystals were taken out by filtration underreduced pressure, vacuum drying, the crystalline body (R) -2- methylpiperazine was 45gacquired. The resulting quality of (R) -2- methylpiperazine of the crystal body, chemical purity of100%, an optical purity of 99.5% e. e. In and, R KaradaOsamuritsu acquisition crystals for (R) -2-methylpiperazine in charge filtrate was 69%. 1, illustrating the steps from Reference Example 1 to Example 1. Was the first crystallizationfrom ( “1 crystallization” was described as) (described as “crystallization”) last crystallization upto six steps. Compared to the Comparative Example 2 step, short process, was able to get a goodoptically active 2-methylpiperazine of easy nature of handling. Thermometer, vacuum stirrer, four-necked flask 1L with a cooling tube equippedfiltrate 330g obtained in Reference Example 1 (in the filtrate of (R)-2-methyl-piperazine 65 g)was concentrated under reduced pressure, (R ) concentration of 2-methyl piperazine was distilledoff the water until the 30 percent. Then, cyclopentyl methyl ether 356g added to theconcentrated solution, mixed solution was heated to normal pressure and azeotroped water andcyclopentyl methyl ether at 8487 C, except for the water. It was then distilled off cyclopentylmethyl ether 205g under reduced pressure. The concentrate was cooled to 47 C, (R) -2-methylpiperazine 0.01g was added as a seed crystal to precipitate crystals, followed by aging for1 hour at 47 C. Was cooled over 5 hours 05 C, and aged for 2 hours at 06 C. Theprecipitated crystals were taken out by filtration under reduced pressure, vacuum drying, thecrystalline body (R) -2- methylpiperazine was 44g acquired. The resulting quality of (R) -2-methylpiperazine of the crystal body, chemical purity of 100%, an optical purity of 99.6% e. e. Inand, R KaradaOsamuritsu acquisition crystals for (R) -2- methylpiperazine in charge filtrate was 68%. Thermometer, vacuum stirrer, four-necked flask 1L equipped with a Dean-Starkapparatus, 33% (S) -2- methylpiperazine solution 300.0g ((S) -2- methylpiperazine 100.0 g,Quality: Chemistry purity 99.9%, optical purity of 80.0% e.e. ) Were charged. Then stirred withtoluene 586.0g (5.86wt times / (S) -2- methylpiperazine). The solution was heated under normalpressure, arms 84 to 87 was azeotroped with water and toluene in C, except for water only.Then, toluene was distilled off 286g under reduced pressure. The concentrate was cooled to4350 C, (S) -2-methylpiperazine 0.01g was added as a seed crystal to precipitate crystals,followed by aging for 1 hour at 4350 C. Then it cooled over 2 hours to 0 to 5 C, and agedfor 2 hours at 05 C. The precipitated crystals were taken out by filtration under reducedpressure, vacuum drying, the crystalline body (S)-2-methylpiperazine 66.8g was obtained (67%yield). The resulting quality of the crystal of (S) -2- methyl piperazine, the chemical p…

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

Reference£º
Patent; TORAY FINE CHEMICALS COMPANY LIMITED; MORII, SEIJI; NISHIKAWA, TAKESHI; (12 pag.)JP2016/37495; (2016); A;,
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.1383146-20-0,(R)-4-(2,4-Dimethoxybenzyl)-3-methylpiperazin-2-one,as a common compound, the synthetic route is as follows.

Synthesis of (R)-l-(2,4-dimethoxybenzyl)-5-ethoxy-6-methyl-l,2,3, 6- tetrahydropyrazine D. Oven dried (115C) sodium carbonate (2.48 g, 23.40 mmol, 2.25 eq.) was placed in a round-bottom flask. The round-bottom flask was backfilled with Ar and then capped with a rubber septum. A solution of (R)-4-(2,4-dimethoxybenzyl)-3-methylpiperazin-2- one C (2.75 g, 10.40 mmol, 1 eq.) in anhydrous DCM (35 mL) was added, followed by freshly prepared triethyloxoniumtetrafluoroborate (2.48 g, 13.05 mmol, 1.25 eq.) in one portion. Thereafter the reaction mixture was stirred further at RT for 45 min to 1 hour, whereupon the reaction mixture was diluted with saturated aqueous NaHC03 (100 mL). The aqueous layer was extracted with DCM (3 x 200 mL). The organic layers were combined, dried over MgS04, filtered and concentrated under reduced pressure to afford 3.1 g of yellow oil. The crude compound was then purified on silica gel (EtOAc/MeOH: 99/1) to afford the desired product D as a pale yellow oil. Yield: 1.44 g, 48 %. LCMS: P = 95 , retention time = 1.8 min, (M+H20+H)+: 311 ; chiral HPLC retention time = 12.3 min, ee > 97 %. 1H-NMR (CDC13): delta 7.23 (d, J= 8.8, 1H), 6.48 (d, J= 8.8, 1H), 6.44 (s, 1H), 4.02 (m, 2H), 3.92 (s, 6H), 3.86 (d, JAB= 14.0, 1H), 3.46 (d, JAB= 14.0, 1H), 3.44 (m, 2H), 3.10 (m, 1H), 2.79 (m, 1H), 2.32 (m, 1H), 1.35 (d, J= 6.8, 3H), 1.24 (t, J= 6.0, 3H)., 1383146-20-0

As the paragraph descriping shows that 1383146-20-0 is playing an increasingly important role.

Reference£º
Patent; EUROSCREEN SA; HOVEYDA, Hamid; DUTHEUIL, Guillaume; FRASER, Graeme; WO2014/154897; (2014); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics