Category: 109-01-3

109-01-3, 1-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

PREPARATION 2 2-(4-methylpiperazin-1-yl)-aniline A mixture of 2-fluoronitrobenzene (6.0 mL, 56.9 mmol) and N-methylpiperazine (8.11 mL, 56.9 mmol) was stirred at 0 C. for 20 minutes, then at room temperature for 3 days. The crude mixture was partitioned between methylene chloride and saturated aqueous sodium bicarbonate and the organic layer was then washed with saturated sodium chloride (NaCl), dried and concentrated in vacuo to provide 2-(4-methylpiperazin-1-yl)-1-nitrobenzene as an orange oil, 12.4 g. 1H-NMR (CDCl3, 300 MHz) delta 7.75 (1H, dd), 7.47 (1 H, dt) 7.15 (1H, dd), 7.03 (1H, dt), 3.09 (1H, dd), 2.56 (1H, dd), 2.36 (3H, s).

109-01-3, 109-01-3 1-Methylpiperazine 53167, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; Pfizer Inc.; US6258953; (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.109-01-3,1-Methylpiperazine,as a common compound, the synthetic route is as follows.

A l-liter-3-neck flask was loaded with 4-nitrobenzoyl chloride (50.5 g, 267 mmol) and THF (500 ml) and cooled to 0 C. Pyridine (44 ml, 544 mmol), then 1-methyl-piperazine (35 ml, 316 mmol) were added while mechanically stirring at 0 C. After the addition was completed the ice bath was removed and the mixture stirred for 1 hour, while warming to room temperature. A voluminous precipitate forms. The slurry was diluted with dichloromethane and 1 M aq. KOH and the layers separated. The organic layer was washed one more time with 1 M aq. KOH, then with brine and dried over MgSO4, filtered and concentrated in vacuum. 31.5 g yellow solid (4-methylpiperazin- l-yl)(4-nitrophenyl)methanone were isolated. MS (ESI) m/z 250 (M+H). 1H NMR (CDCl3) delta ppm 8.27 (d, 2 H, J= 7.9), 7.56 (d, 2 H, /= 7.9), 3.81 (bs, 2 H), 3.37 (bs, 2 H), 2.50 (bs, 2H), 2.34 (bs, 2H), 2.32 (s, 3H)., 109-01-3

The synthetic route of 109-01-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; PURANDARE, Ashok, Vinayak; BATT, Douglas, G.; LIU, Qingjie; JOHNSON, Walter, L.; MASTALERZ, Harold; ZHANG, Guifen; ZIMMERMANN, Kurt; WO2010/80474; (2010); 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.109-01-3,1-Methylpiperazine,as a common compound, the synthetic route is as follows.

The [4-CHLORO-3-CYANO-6-METHOXY-7- [3- (4-METHYLPIPERAZIN-1-YL)] propoxy] quinoline used as a starting material was prepared as follows:- A mixture of 3-bromopropanol (20 ml), [N-METHYLPIPERAZINE] (29 ml), potassium carbonate (83 g) and ethanol (200 ml) was stirred and heated to reflux for 20 hours. The mixture was cooled to ambient temperature and filtered. The filtrate was evaporated and the residue was triturated under diethyl ether. The resultant mixture was filtered and the filtrate was evaporated. The residue was purified by distillation at about [60-70C] under about [0.] 2 mm Hg to give [1- (3-HYDROXYPROPYL)-4-METHYLPIPERAZINE] (17 g); NMR Spectrum: (CDC13) 1.72 (m, 2H), 2.3 (s, 3H), 2.2-2. [8] [(M,] 8H), 2.6 (t, 2H), 3.8 (t, 2H), 5.3 (br s, 1H).

109-01-3, 109-01-3 1-Methylpiperazine 53167, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/5284; (2004); 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.109-01-3,1-Methylpiperazine,as a common compound, the synthetic route is as follows.

A mixture [OF N-METHYLPIPERAZINE] (0. [0499MOL),] [2-BROMOETHANOL] (0. [0749MOL)] and [K2CO3] (0. [0998MOL)] in 2-butanon (90mL) was stirred for [4H] at [90¡ãC.] The cooled reaction mixture was filtered. The filtrate was evaporated. Yielding 90percent of intermediate 14. (Remark: lower yields were obtained on [A] higher scale and purification by short column chromatography was necessary)., 109-01-3

The synthetic route of 109-01-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; JANSSEN PHARMACEUTICA N.V.; WO2004/7498; (2004); A2;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

109-01-3, 1-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A reaction mixture of 54 5-fluoro-2-nitroanisole (1.5 g, 8.7 mmol), 55 1-methylpiperazine (1.0 g, 10.5 mmol) and 56 potassium carbonate (2.4 g, 17.4 mmol) in 40 N,N-dimethylformamide (DMF, 5 mL) was heated to 80 C. for 18 hours, and after cooling to room temperature, 50 mL 48 water was poured into the reaction, and filtered to give the precipitate, which was used directly in the next step. Under a hydrogen atmosphere, the precipitate was dissolved in 30 mL 43 methanol, 57 Raney nickel (200 mg) was added, and the mixture was reacted under the hydrogen atmosphere at room temperature for 5 hours. After filtration, the filtrate was collected and purified by column chromatography to give the product 58 2-methoxy-4-(4-methylpiperazin-1-yl)aniline 1.6 g, yield 85%. LC-MS(APCI): m/z=221.3 (M+1)., 109-01-3

The synthetic route of 109-01-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Shenzhen TargetRx, Inc.; Wang, Yihan; Ren, Xingye; Jin, Jian; Li, Huanyin; Ai, Yixin; (162 pag.)US2019/152954; (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.109-01-3,1-Methylpiperazine,as a common compound, the synthetic route is as follows.

A solution of 4-nitrobenzoyl chloride (25) (1 g, 5.39 mol) in CH3CN (50 mL) was treated with 1-methylpiperazine (26) at 10 C. over 10 min. The reaction mixture was stirred for another 1 h followed by addition of TEA (1.49 mL, 2 eq) and stirring for an additional half hour. The reaction mixture was diluted with ice-cold water (150 mL) and extracted with EtOAc (4¡Á150 mL). The organic layer was dried over MgSO4 and concentrated to give 1.1 g (82% yield) (4-methylpiperazin-1-yl)(4-nitrophenyl)methanone 27 as a yellow solid. TLC: 10% MeOH/DCM, Rf=0.6. 1NMR (400 MHz, CDCl3) 8.28(d, J=8.5 Hz, 2H), 7.56(d, J=8.5 Hz, 2H), 3.88(br-s, 4H), 3.46(br-s, 4H), 2.40(s, 3H) ESI/MS m/z 250.0 (M+H)

109-01-3, 109-01-3 1-Methylpiperazine 53167, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; SUPERGEN, INC.; US2008/214558; (2008); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

109-01-3, 1-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of (3-bromophenyl)methanol (570 mg, 3.05 mmol) in THF (5 mL) was added LHMDS (7.43 mL, 7.43 mmol) and the mixture was stirred at RT for 30 minutes. Ru-phos precatalyst (97 mg, 0.133 mmol), dicyclohexyl(2′,6′-diisopropoxy-[l,l’- biphenyl]-2-yl)phosphine (61.9 mg, 0.133 mmol), and 1-methylpiperazine (0.441 mL, 3.98 mmol) were added, the mixture was degassed with a stream of nitrogen and heated to 75 C for 1 h. The mixture was then diluted with DCM and washed with water. The organic layer was concentrated under reduced pressure and the residue was purified by Si02gel chromatography (0-20% MeOH in DCM) to give the title compound (506 mg, 80%). MS(ES+) C12H18N20 requires: 206, found: 207 [M+H]+.

109-01-3, 109-01-3 1-Methylpiperazine 53167, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; JONES, Philip; DIFRANCESCO, Maria, Emilia; PETROCCHI, Alessia; MARSZALEK, Joe; LIU, Gang; KANG, Zhijun; CARROLL, Christopher, L.; MCAFOOS, Timothy; CZAKO, Barbara; WO2014/31928; (2014); A2;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

109-01-3, 1-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A 100 mL 3-necked flask was equipped with a magnetic stirrer bar, nitrogen in- and outlet and septum. The setup was thoroughly dried using a heat gun and allowed to cool to room temperature under a nitrogen flow. Then, 4-nitrobenzoyl chloride (4.64 g, 25.0 mmol) was dissolved in dry dichloromethane (50 mL) and the solution was 10 minutes in an ice-water bath. N-methylpiperazine (2.58 g, 25.8 mmol, 1.03 eq) was added drop wise over a 10 minute time interval while stirring vigorously. The resulting suspension was stirred for 1 hour at 0 C., after which triethylamine (5.01 g, 50.0 mmol, 2.0 eq) was added and stirrring was continued at r.t. for 1 h. The reaction mixture was transferred into a separatory funnel and washed with demineralized water (3¡Á50 mL). The organic layer was dried over Na2SO4, filtered over a paper filter and all volatiles were removed under reduced pressure using a rotary evaporator to give the desired product as a pale orange solid (5.77 g 23.1 mmol, 92%)., 109-01-3

The synthetic route of 109-01-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; TEIJIN ARAMID B.V.; VAN DEN HEUVEL, Christiaan J.M.; VELD, Martijn Arnoldus Johannes; QUAIJTAAL, Joannes H.M.; VERHOEF, Rene P.; DE JONG, Jorrit; NIJENHUIS, Wido; (12 pag.)US2018/223077; (2018); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

109-01-3, 1-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

109-01-3, 1-METHYLPIPERAZINE (13.49 g, 135 mmol) and triethylamine (16.4 g, 162 mmol) were added to 200 mL OF CHC13 in a 500 mL round-bottomed flask equipped with a 250 mL addition funnel under argon with a magnetic stirring bar. 4-nitrobenzoyl chloride (25.00 g, 135 mmol) was dissolved in 200 mL OF GHCI3 with slight warming. The solution of benzoyl chloride was placed in the addition funnel and was added slowly to the solution of piperazine. The solution warmed slightly and was allowed to stir 1 hour after the addition was complete. The reaction was concentrated until the product began to precipitate. The product was isolated by vacuum filtration and rinsed with two 25 mL portions of cold diethyl ether. After recrystallization from 95% ethanol, the product, 4-METHYL-1- (4- nitrobenzoyl) piperazine, was pure by standard analytical techniques.

As the paragraph descriping shows that 109-01-3 is playing an increasingly important role.

Reference£º
Patent; SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH; WO2004/63195; (2004); 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.109-01-3,1-Methylpiperazine,as a common compound, the synthetic route is as follows.

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…

109-01-3, 109-01-3 1-Methylpiperazine 53167, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; MIKANA THERAPEUTICS, INC.; WO2006/88949; (2006); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics