Category: piperazines

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.13484-40-7,1-(2-Methoxyethyl)piperazine,as a common compound, the synthetic route is as follows.

EXAMPLE 11; Preparation of (N-(2-aminophenyl)-4-{3-methyl-5-[(4-(2-methoxyethyl)-piperazin-1-yl)methyl]pyridin-2-yl}benzamide); tert-Butyl (2-{[4-(5-formylpyridin-2-yl)benzoyl]amino}phenyl)carbamate (0.20 g, 0.4634 mmol; prepared as described in method 3), 1-(2-methoxyethyl)-piperazine (104 mg, 0.7 mmol) and acetic acid (27 mul, 0.4634 mmol) were dissolved in tetrahydrofuran (5 ml). The mixture was stirred at ambient temperature for 1 hour then sodium triacetoxyborohydride (147 mg, 0.695 mmol) added and the mixture stirred for a further 16 hours. The mixture was concentrated and partitioned between dichloromethane (5 ml) and saturated sodium bicarbonate (5 ml). The organics were washed with further saturated sodium bicarbonate (2¡Á5 ml) and brine (5 ml) then dried over magnesium sulphate and filtered. This solution was then treated with trifluoroacetic acid (1.0 ml) and the solution then stirred at ambient temperature for 2 hours. The resulting solution was absorbed onto an SCX-2 column, which was washed with methanol (3 column volumes) and the product eluted with a 2M solution of ammonia in methanol (3 column volumes) which was concentrated to give the product as a gum. The residue was purified by acid modified reverse phase HPLC. Fractions containing the product were absorbed onto an SCX-2 column and washed with methanol (2 column volumes) then the products eluted with a 2M solution of ammonia in methanol (2 column volumes) and concentrated under reduced pressure, to give a residue which was triturated with ether to give title compound as a solid (12 mg, 6%). NMR Spectrum: (DMSO-d6); 2.37 (s, 3H), 2.43 (m, 10H), 3.24 (s, 3H), 3.43 (t, 2H), 3.53 (s, 2H), 4.92 (s, 2H), 6.62 (m, 1H), 6.80 (m, 1H), 6.99 (m, 1H), 7.21 (m, 1H), 7.66 (s, 1H), 7.69 (d, 2H), 8.07 (d, 2H), 8.42 (m, 1H), 9.72 (s, 1H). Mass Spectrum: M+H+460., 13484-40-7

13484-40-7 1-(2-Methoxyethyl)piperazine 2734638, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; ASTRAZENECA AB; US2008/119451; (2008); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

129799-15-1, Methyl 1-Boc-piperazine-2-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Piperazine-1, 2-dicarboxylic acid, 1-TERT-BUTYL ester, 2- methyl ester (250 mg, 1.03 mmol) was added dropwise to a stirred solution of 4-bromobenzenesulfonyl chloride (290 mg, 1.14 mmol) and pyridine (1 mL) in anhydrous 1,2-dichloroethane (10 mL) at room temperature. The reaction mixture was stirred for 1 hr (TLC control) and then poured into water (25 mL) and extracted with diethyl ether (3 x 25 mL). The combined extract was washed with water (2 x 10 mL), brine (3 x 10 mL), dried over anhydrous MGS04, filtered and concentrated in vacuo. Purification of the product by flash column chromatography, using 40 % ethyl ACETATE/HEXANE as eluent, afforded the title compound as a white foam (350 mg, 74 %).

129799-15-1, 129799-15-1 Methyl 1-Boc-piperazine-2-carboxylate 2756818, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; THE INSTITUTE OF PHARMACEUTICAL DISCOVERY, LLC; WO2004/99192; (2004); A2;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

70261-82-4, 4-(4-Methylpiperazin-1-ylmethyl)phenylamine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,70261-82-4

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…

The synthetic route of 70261-82-4 has been constantly updated, and we look forward to future research findings.

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

5464-12-0, 1-(2-Hydroxyethyl)-4-methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5464-12-0, General procedure: The mixture of mollugin (0.35 mmol), alcohol (3.52 mmol), and catalytic p-TsOH (0.035 mmol) in2 mL microwave vial was placed in the cavity of microwave reactor, and then stirred for 3 h at 160 ¡ãC.The produced brown mixture was dried under vacuum and subjected to purification (20 g silica gelcartridge, dichloromethane-MeOH) to give the title product.

The synthetic route of 5464-12-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Hong, Ki Bum; Kim, Darong; Kim, Bo-Kyung; Woo, Seo Yeon; Lee, Ji Hoon; Han, Seung-Hee; Bae, Gyu-Un; Kang, Soosung; Molecules; vol. 23; 8; (2018);,
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.129799-15-1,Methyl 1-Boc-piperazine-2-carboxylate,as a common compound, the synthetic route is as follows.

Piperazine-1, 2-dicarboxylic acid, 1-tert-butyl ester, 2- methyl ester (250 mg, 1.03 mmol) was added dropwise to a stirred solution of 4-bromobenzoyl chloride (250 mg, 1.14 mmol), triethylamine (0.43 mL, 3.09 mmol) and DMAP (5 mg) in anhydrous 1,2-dichloroethane (10 mL) at room temperature. The reaction mixture was stirred for 2 hrs (TLC control) and then poured into water (25 mL) and extracted with diethyl ether (3 x 25 mL). The combined extract was washed with water (2 x 10 mL), brine (3 x 10 mL), dried over anhydrous MGS04, filtered and concentrated in vacuo. Purification of the product by flash column chromatography, using 40 % ethyl acetate/hexane as eluent, afforded the title compound as a white foam (310 mg, 71 %)., 129799-15-1

129799-15-1 Methyl 1-Boc-piperazine-2-carboxylate 2756818, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; THE INSTITUTE OF PHARMACEUTICAL DISCOVERY, LLC; WO2004/99192; (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.39539-66-7,4-Methylpiperazine-1-carbonyl chloride,as a common compound, the synthetic route is as follows.

To a solution of the bromo methyl seco compound (0.074 mMoles) in 3 mL DMF was added the 5-actyl indole-2-carboxylate (30 mg, 0.15 mMoles) and EDC (28 mg, 0.15 mMoles) and the resulting mixture was stirred overnight. The reaction mixture was concentrated and purified by silica gel chromatography using 5% MeOH in DCM Tt give 29 mg (74 % yield) of product which was confirmed by mass spec M+1 = 523. To a solution of the compound synthesized in step C in 5 mL DCM and 300 muL allyl alcohol was added methyl piperazine carbonyl chloride (22 mg, 0.11 m Moles) and pyridine 44 muL. The reaction mixture was stirred at room temperature for 5 hours. Concentration followed by purification by silica gel chromatography using 5 % MeOH/DCM as eluant gave 48 mg of the desired product (73 % yield). The product was confirmed by Mass Spec. M+1 = 650. A solution of the above compound (8.2 mg , 0.012 mmoles) and Mal-PEG4-hydrazine in 5 % acetic acid in anhydrous DCM was stirred at room temperature for 20 minutes followed by evaporation of Solvents and Reverse phase Prep HPLC using acetonitrile and ammonium formate buffered aqueous phase gave 2.5 mg of the desired final product which was confirmed by mass Spec, M+1 = 1063

39539-66-7, 39539-66-7 4-Methylpiperazine-1-carbonyl chloride 3016935, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; MEDAREX, INC.; WO2005/112919; (2005); 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.694499-26-8,4-((4-Methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)aniline,as a common compound, the synthetic route is as follows.,694499-26-8

5-Bromo-6-methyl – nicotinic acid (0.20 g, 0.93 mmol) and 4-(4-methyl – piperazinyl small-ylmethyl) -3-trifluoromethyl – phenylamine (0.23g, 0.85 mmol ) was dissolved in N, N- dimethylformamide (10 mL), were addedunder ice-cooling 2 – (; 7-aza-benzotriazole) -Nu, Nu, Nu ‘, Nu’- tetramethylhexafluorophosphate (0.39 g, 1.02 mmol) and diisopropylethylamine (0.20 mL,1.27 mmol), and stirring was continued overnight. The reaction mixture waspoured into water, extracted with ethyl acetate, the organic phaserespectively, 5% dilute hydrochloric acid, saturated sodium bicarbonatesolution, washed with water and saturated brine, dried over anhydrous sodiumsulfate, and concentrated under reduced pressure, silica gel columnchromatography to give 5-bromo-6-methyl -N- [4- (4- methyl -piperazin-1-ylmethyl) -3-trifluoromethyl – phenyl] – nicotinamide (yellowsolid, 0.26 g ), yield 65%.

694499-26-8 4-((4-Methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)aniline 46838908, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; Shanghai Pharmaceuticals Holding Co.,Ltd .; WAN, HUIXIN; LI, CHUNLI; SHI, Chen; Liu, Haiyan; Li, Ping; XIA, Guangxin; HAN, Yanan; (52 pag.)CN103420977; (2016); B;,
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76003-29-7,76003-29-7, 1-Boc-3-Oxopiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Will be 49.94mmol3-oxo-1-piperazinecarboxylic acid tert-butyl ester1 dissolved in 100 mL of tetrahydrofuran,Add 51.4 mmol of 60% NaH to the temperature below zero, stir for 30 minutes, then add 25.5 mL of ethyl bromide and reflux for 3 hours.It was quenched by cooling with water, extracted with ethyl acetate and dried.Spin dry to obtain 10.8 g of compound 2, the recovery of compound 2 was 95%;

The synthetic route of 76003-29-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Shanghai Changtai Biological Technology Co., Ltd.; Lu Qian; Kuang Yi; Li Guohua; (9 pag.)CN108822048; (2018); A;,
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.34334-28-6,4-(4-Methylpiperazin-1-yl)benzonitrile,as a common compound, the synthetic route is as follows.

4-Fluorobenzonitrile (12 g, 99 mmol, 1 eq.) and 100 mL of DMF are placed in a 250 mL round-bottomed flask. N-Methylpiperazine (16 mL, 1.6 eq., 123 mmol) is added to this solution. The orange solution is heated at a temperature in the region of 90 C. for 15 hours. The solvent is then evaporated to dryness and the residue is diluted with 500 mL of diethyl ether. The solution is washed with sodium hydrogen carbonate solution (2*100 mL) and then with saturated sodium chloride solution (100 mL). After evaporation, the 4-(4-methylpiperazin-1-yl)benzonitrile (orange solid, 10 g, 77%) is used without further purification in the following hydrolysis step. It is added at a temperature in the region of 0 C. to a solution of 98% sulfuric acid (25 mL) and 5 mL of water. The purple solution is then heated at a temperature in the region of 100 C. for 8 hours. The solution is cooled and then hydrolyzed by pouring onto ice. The pH is adjusted to 9-10 with sodium hydroxide pellets. The precipitate obtained is filtered off and washed thoroughly with water and then with tetrahydrofuran, which partially dissolves the product. The water is separated out by settling. After evaporating the organic phase to dryness, a solid is obtained, which is purified by chromatography on silica gel, eluding with a methanol/dichloromethane mixture (15/85 by volume). 4-(4-Methylpiperazin-1-yl)benzamide (8.7 g, 80%) is thus obtained in the form of a white solid, which is used directly in the following step., 34334-28-6

The synthetic route of 34334-28-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Aventis Pharma S.A.; US2008/146542; (2008); 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.129799-08-2,1-tert-Butyl 3-methyl piperazine-1,3-dicarboxylate,as a common compound, the synthetic route is as follows.

[0253] 4-(fe/7-Butoxycarbonyl)-l-(4-(tert-butoxycarbonyl)-l-(4-((4-((8A,l 1/?,13L’,- 14L’, 1 IS)- 17-hyd roxy- 13-methy 1-3-oxo- 17-(p rop- 1 -yn-1 -yl)- 2,3,6,7,8,ll,12,13,14,15,16,17-dodecahydro-l -cyclopenta[fl]phenanthren-ll- yl)phenyl)(methyl)amino)butanoyl)piperazine-2-carbonyl)piperazine-2-carboxylic acid (0380) To a solution of Intermediate C (132 mg, 0.263 mmol) and 1 -(tert-butyl) 3-methyl piperazine-l,3-dicarboxylate in DMF (1 ml) were added iPnNEt (0.092 ml, 0.526 mmol) and HATU (110 mg, 0.289 mmol) and the resulting mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with EtOAc (20 mL) and washed with sat NH4CI (20 mL), water (20 mL x 3), and brine (20 mL). The organic layer was dried over Na2S04, filtered and concentrated under reduced pressure. The residue was dissolved in 1.0 mL of THF and 0.4 mL of water and treated with LiOH and stirred at room temperature for 1 hour. The residue was purified by reverse phase preparative HPLC (Mobile phase: A = 0.1% TFA/H2O, B = 0.1% TFA/MeCN; Gradient: B = 10 – 90%; 20 min) to give the title compound (13.1 mg, 0.014 mmol, 5.38 % yield) as a brown amorphous material.

129799-08-2, 129799-08-2 1-tert-Butyl 3-methyl piperazine-1,3-dicarboxylate 2756819, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; LINK, James, T.; LISSANU DERIBE, Yonathan; (91 pag.)WO2019/200217; (2019); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics