Heterocyclic Building Blocks-piperazine

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.

192130-34-0, Method B. (i) In a 100 mL three-neck round-bottom flask was charged 2-chloronicotinic acid 1 (0.3151 g, 2.0 mmol), HOBt (0.4054 g, 3.0 mmol), and EDAC (0.5751 g, 3.0 mmol) were dissolved in CH 2 Cl 2 (10 mL). After stirring for 10 min, 4-(2-aminoethyl)-1-boc-piperazine (0.4586 mL, 2.0 mmol) was added followed by Et 3 N (0.5733 mL, 4.0 mmol) and the reaction mixture stirred at room temperature for 16 h. After completion of the reaction, the solution was washed with water (30 mL), and the product was extracted with CH 2 Cl 2 (3 X 20 mL). The combined organic phases were washed with brine, and dried over anhydrous Na 2 SO 4 , filtered, and concentrated under reduced pressure. The concentrated crude oil tert-butyl 4-(2-(2-chloronicotinamido)ethyl)piperazine-1-carboxylate intermediate was obtained (0.63 g, 1.71 mmol, 86%). The product was used in the next step without further purification. Step (ii) In a 100 mL three neck round bottom flask equipped with a stirring bar and reflux condenser, tert-butyl 4-(2-(2 chloronicotinamido)ethyl)piperazine-1-carboxylate (0.630 g, 1.71 mmol) and 9-ethyl-9H-carbazol-3-amine (0.0361 g, 1.72 mmol) were dissolved in 5 mL of DMSO. To the solution, CuI (0.0651 g, 0.3 mmol) and Cs 2 CO 3 (1.11 g, 3.42 mmol) were added and heated at 90 C for 24 hr. After the reaction was complete (analyzed by TLC), the mixture was allowed to reach room temperature. The mixture was washed with water (30 mL), and extracted with CH 2 Cl 2 (3 X 30 mL). The combined organic phases were washed with brine and dried over anhydrous Na 2 SO 4 , filtered, and concentrated under reduced pressure. The crude oil was purified via column chromatography over silica gel and the product 4b was obtained as a white solid (0.08g, 0.15 mmol, 9%). TLC analysis in CH 2 Cl 2 -MeOH (9:1), R f =0.44. 1 H NMR (400 MHz, CDCl 3 ) delta 1.26 (4H, t, J = 7.1 Hz), 1.42 (3H, t, J = 7.3 Hz), 1.46 (9H, s), 1.65 (3H, s), 2.04 (2H, s), 2.48 (3H, t, J = 4.6 Hz), 2.65 (2H, t, J = 5.9 Hz), 3.47 (4H, t, J = 5.3 Hz), 3.56 (2H, q, J = 5.6 Hz), 4.11 (1H, q, J = 7.1 Hz), 4.34 (2H, q, J = 7.6 Hz) 6.64(1H, q, J = 4.8 Hz), 7.19 (1H, t, J = 6.3 Hz), 7.26 (1H, s,), 7.35 (1H, d, J = 4.3 Hz), 7.39 (1H, d, J = 3.8 Hz), 7.43 (1H, t, J = 7.6 Hz), 7.65 (1H, d, J = 1.8 Hz), 7.67 (1H, t, J = 2.3 Hz), 7.69 (1H, d, J = 2.0 Hz), 8.08 (1H, d, 7.6 Hz), 8.31 (1H, d, J = 1.5 Hz), 8.32 (1H, d, J = 1.8 Hz), 8.33 (1H, d, J = 2.0 Hz), 10.40 (1H, s); 13 C NMR (100 MHz, CDCl 3 ) delta 13.8, 37.5, 42.2, 44.8, 45.5, 66.6, 108.3, 112.8, 115.3, 118.3, 120.5, 120.7, 122.8, 123.2, 125.4, 131.6, 132.8, 136.5, 132.0, 140.3, 147.6, 167.8. GC-MS m/z (rel%): [M] 542 (0.01), [M-C 17 H 19 N 3 O] 281 (67.5), [M-C 12 H 23 N 3 O 3 ] 257 (2.6), [M-C 11 H 17 N 3 O] 207 (100).

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
Article; Vlaar, Cornelis P.; Castillo-Pichardo, Linette; Medina, Julia I.; Marrero-Serra, Cathyria M.; Velez, Ericka; Ramos, Zulma; Hernandez, Eliud; Bioorganic and Medicinal Chemistry; vol. 26; 4; (2018); p. 884 – 890;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

148546-99-0, 3-(4-Methylpiperazin-1-yl)aniline is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1-Chloro-3-nitro-benzene (1.0 g, 7 mmol) is mixed with 1-methyl-piperazine (2.0 mL) and the reaction is capped and stirred at 190 C. for 2 hours. After reaction, the excess 1-methyl-piperazine is removed by rotary evaporation to give the crude product as yellow oil. The crude product is purified by silica gel flash column to give 1.2 g of 1-methyl-4-(3-nitro-phenyl)-piperazine (yield 78%). The 1-methyl-4-(3-nitro-phenyl)-piperazine (1.2 g, 5.4 mmol) is dissolved in methanol (50 mL) and Pd/C (5%, 120 mg) is added to the solution. A hydrogen balloon is attached to the flask. The solution is stirred overnight at room temperature. After the reaction is complete, the Pd/C is filtered and the filtrate collected and concentrated by rotary evaporation, to give 3-(4-methyl-piperazin-1-yl)-phenylamine. 2-Fluoro-6-chloro-9-phenyl-9H-purine (50 mg, 0.20 mmol), 3-(4-methyl-piperazin-1-yl)-phenylamine (42 mg, 0.22 mmol) and diisopropylethylamine (35 muL, 0.2 mmol) are mixed in 1-butanol (0.4 mL). The reaction is stirred at 80 C. for 2 hours before adding trans-1,4-cyclohexanediamine (68 mg, 0.6 mmol) and diisopropylethylamine (70 muL, 0.4 mmol). The reaction mixture is stirred at 110 C. overnight. The solvent is removed by rotary evaporation and the crude product is redissolved in DMSO and purified by HPLC to give N2-(4-amino-cyclohexyl)-N6-[3-(4-methyl-piperazin-1-yl)-phenyl]-9-phenyl-9H-purine-2,6-diamine as a white powder; 1H NMR 400 MHz (DMSO-d6) delta 9.12 (s, 1H), 8.16 (s, 1H), 7.78 (d, 2H, J=6.0 Hz), 7.58 (d, 1H, J=7.6 Hz), 7.42 (m, 2H), 7.24 (m, 2H), 7.00 (t, 1H, J=8.0 Hz), 6.48 (m, 2H), 3.53 (s, 1H), 3.25 (m, 4H), 3.01 (t, 4H, J=4.8 Hz), 2.09 (s, 3H), 1.74 (m, 2H), 1.66 (s, 2H), 0.92 (m, 4H), 0.79 (t, 1H, J=7.2 Hz); MS m/z 498.3 (M+1)., 148546-99-0

The synthetic route of 148546-99-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; IRM LLC; US2005/124637; (2005); 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

[2-CHLOROPYRIMIDINE] (1.14 g, 10.0 mmol), 2-methylpiperazine (1.20 g, 12.0 mmol), and triethylamine (1.52 g, 15 mmol) were dissolved in 10 mL of chloroform and the resulting mixture was stirred at room temperature, about [25C,] for 4 hours. The reaction was quenched with water and the resulting mixture was extracted with chloroform. The organic layer was dried, concentrated, and purified using a silica gel column eluted with gradient elution from ethyl acetate to 2/1 ethyl acetate/methanol to provide Compound O as a yellow oil (95% yield). [A] solution of Compound O (178 mg, [1.] 0 mmol), Compound F (219 mg, 1.5 [MMOL),] HOBt (203mg, 1.5 mmol), and DIC (189 mg. [1.] 5 mmol) in 4.5 [ML] dichloromethane (“DCM”) was stirred at room temperature, about [25C,] for 4 hours. After evaporation, the product was purified using a silica gel column eluted with gradient elution from hexane to 1/1 hexane/ethyl acetate to provide 153 mg of Compound AFX [(IIB)] as a slight yellowish solid (50% yield). The structure of Compound AFX [(IIB)] was confirmed [BY’H NMR] and mass spectral [(MS)] analysis. Compound AFX [(IIB)] [:’H] NMR [(CDC13)] 8 8.35 (d, J = 4.7 Hz, 2H), 7.61 (m, 2H), 7.40 [(M,] 3H), 6. [55] (dd, J = 4.7, 4.7 Hz, [1H),] 4.91 [(M,] [0. 6H),] 4. 78 (m, 2H), 4.63 (dt, J = 1.8, 11. [6 HZ,] 0.4H), 4.52 (d, [J = 13. 3 HZ,] 0.4H), 4.33 (d, [J = 13. 3 HZ,] 0.6H), 3.59 [(M,] 0.6H), 3.20 (m, 2.4H), 1.36 (d, J = 6.8 Hz, 1.2H), 1.25 (d, [J =] 6.8 Hz, 1.8H) ; MS [(EL)] : m/z 329 [(M+NA+).]

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

Reference£º
Patent; Euro-Celtique, S.A.; WO2004/29044; (2004); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

154590-35-9, tert-Butyl 4-(4-amino-2-fluorophenyl)piperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 3-fluoro-4- (N-t-butoxycarbonylpiperazin-1-yl) aniline (16.8 g, 57 mmol) (obtained according to the procedure described in preparation 3) in THF (30 ml), dimethyl aniline (7.92 ml, 62. 7 mmol) was added. To this benzyl chloroformate (8.27 ml, 58. 14 mmol) dissolved in THF (20 ml) was added over a period of 20 min upon stirring at 0 C. After completion of the reaction, the resulting mixture was quenched with saturated NaCl solution (50 ml) and extracted with EtOAc (3 x 200 ml). The organic layer was evaporated, dried over Na2S04 and purified using silica gel column using 50% EtOAc in hexane to afford the title compound (24 g).

154590-35-9, 154590-35-9 tert-Butyl 4-(4-amino-2-fluorophenyl)piperazine-1-carboxylate 16203630, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; Orchid Chemicals &amp Pharmaceuticals Ltd; WO2004/18439; (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.115761-79-0,1-(2,4-Difluorophenyl)piperazine,as a common compound, the synthetic route is as follows.

5-(4-Fluorophenyl)-5-methyl-3-(oxiran-2-ylmethyl)imidazolidine-2,4-dione 17 (3.5 mmol, 1.2 eq) with appropriate piperazine derivative (3.0 mmol, 1.0 eq) in 50 mL flat-bottom flask were irradiated in household microwave: 300 MW (1 min), 450 MW (1 min), 300 MW (2 min). Progress of reaction was controlled by TLC (DCM/MeOH 95:5). Pure products were obtained from crude glue-reactants after microwave reaction by: crystallization from methanol (Method A), column chromatography with DCM/MeOH (98:2) as eluent (Method B) and/or dissolving in ethanol and saturating with gaseous HCl to provide product in form of hydrochloride (Method C)., 115761-79-0

As the paragraph descriping shows that 115761-79-0 is playing an increasingly important role.

Reference£º
Article; Kucwaj-Brysz, Katarzyna; Warszycki, Dawid; Podlewska, Sabina; Witek, Jagna; Witek, Karolina; Izquierdo, Andrea Gonzalez; Sata?a, Grzegorz; Loza, Maria I.; Lubelska, Annamaria; Latacz, Gniewomir; Bojarski, Andrzej J.; Castro, Marian; Kie?-Kononowicz, Katarzyna; Handzlik, Jadwiga; European Journal of Medicinal Chemistry; vol. 112; (2016); p. 258 – 269;,
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Piperazines – an overview | ScienceDirect Topics

314741-40-7, (S)-tert-Butyl 3-(hydroxymethyl)piperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

INTERMEDIATE 5 (S)-(4-Methyl-piperazin-2-yl)-methanolTo a stirred suspension of (S)-piperazine-l,3-dicarboxylic acid l-tert-buty ester (5.00 g, 21.7 mmol) in THF (40 mL) was slowly added 1.0 M borane-THF complex solution (32.6 rnL, 32.6 mmol). The reaction was heated to 90 0C and stirred under reflux for 2 hours. The reaction mixture was removed from the heat before a further 1.5 equivalents of 1.0 M borane-THF complex solution (32.6 mL, 32.6 mmol) was added. The reaction was reheated to 90 0C and stirred under reflux for a further 2 hours. The reaction was cooled to 0 0C and quenched by the slow addition of MeOH. The reaction mixture was then concentrated in vacuo. The white solid obtained was dissolved in THF (30 mL), cooled to 0 0C and slowly added a 2.0M solution of LiAlH4 in THF (27 mL, 54.0 mmol). The reaction was heated to 90 0C and stirred under reflux for 2h. A further portion of 2.0M solution of LiAlH4 in THF (27 mL, 54.0mmol) was added and the reaction stirred under reflux for 4h and then at room temperature overnight. The reaction mixture was cooled to O0C and quenched by the slow addition of 1.0M aq NaOH solution until the exothermic reaction subsided. The resulting gel was diluted with THF and the solids filtered off. The filtrate was then concentrated in vacuo to afford (S)-(4-methyl-piperazin-2-yl)-methanol (2.84 g, 101% crude yield) as a colourless oil., 314741-40-7

314741-40-7 (S)-tert-Butyl 3-(hydroxymethyl)piperazine-1-carboxylate 24820294, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; BIOVITRUM AB (PUBL); WO2009/71658; (2009); A1;,
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31166-44-6, 1-Cbz-Piperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,31166-44-6

Step 1 Preparation of Compound 132To a suspension of NaOt-Bu (3.73 g, 38.9 mmol), Pd(dba)2 (0.298 g, 0.518 mmol), RuPhos (0.484 g, 1.036 mmol) and 2-bromo-l,4-difluorobenzene (5 g, 25.9 mmol) in Toluene (50 ml) was added benzyl piperazine-l-carboxylate (6.00 ml, 31.1 mmol) at r.t. under N2.The mixture was stirred at 100¡ãC under N2 for 1 hr. The reaction mixture was diluted with H20 and AcOEt at r.t., then the resulting solid was filtered, rinsed with AcOEt and H2O.The filtrate was extracted with AcOEt x 2. The organic layers were combined and washed with brine. The organic layer was dried over MgS04, filt and cone. The crude product was added to a silica gel column and was eluted with AcOEt-Hexane. Collected fractions were evaporated. The residual oil was triturated with CH2C12-Hexane, then filtered, rinsed with Hexane to afford compound 132 (3.7 g, 43.0 percent) as a white solid.1H-NMR (CDC13) delta: 7.40-7.29 (5H, m), 7.01-6.89 (1H, m), 6.66-6.56 (2H, m), 5.16 (2H, s), 3.67 (4H, t, J= 5.1 Hz), 3.11-2.97 (4H, m).

As the paragraph descriping shows that 31166-44-6 is playing an increasingly important role.

Reference£º
Patent; Shionogi & Co., Ltd.; KUROSE, Noriyuki; WO2011/162409; (2011); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

162046-66-4, 4-(4-(tert-Butoxycarbonyl)piperazin-1-yl)benzoic acid is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a mixture of 4-(4-carboxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (250 mg, 0.82 mmol) and 2-aminothiazole (125 mg, 0.83 mmol) in DMF (20 mL) was added EDCl (184 mg, 0.96 mmol) and DMAP (100 mg, 0.83 mmol). The mixture was stirred at room temperature overnight and then heated to 100 C. for 5 hrs. Solvents were evaporated and the residue was extracted with ethyl acetate and ammonium chloride solutions. The residue was crystallized from methanol (40 mL) to afford the intermediate 4-[4-(benzothiazol-2-ylcarbamoyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester. LCMS calc for C23H26N4O3S (m/e) 438.17, obsd 439.2 (M+H).The above intermediate was then suspended in methylene chloride (3 mL) and treated with trifluoroacetic acid (1 mL). The mixture was stirred at room temperature for 1 hr and then the solvents were evaporated. The residue was dried, triturated with ether and filtered to afford N-benzothiazol-2-yl-4-piperazin-1-yl-benzamide trifluoroacetate (130 mg) MS calc for C18H18N4OS (m/e) 338., obsd 339. (M+H)

162046-66-4, The synthetic route of 162046-66-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Bolin, David Robert; Cheung, Adrian Wai-Hing; Hamilton, Matthew Michael; Marcopulos, Nicholas; McDermott, Lee Apostle; Qian, Yimin; US2010/113782; (2010); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

21416-67-1, 4,4′-(Propane-1,2-diyl)bis(piperazine-2,6-dione) is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

At the beginning of each working day the capillary was flushed with NaOH 0.1M for 10min, 5min with Milli-Q water and 40min with the buffer in basic conditions and with MeOH for 5min, NaOH 1M for 25min, 5 min with Milli-Q water, 5min with HCl 0.1M and 30min with the buffer in acid conditions. In order to ensure the repeatability between injections, the capillary was flushed with NaOH 0.1M for 5min, 5min with the buffer and 2min with the BGE in basic or acid conditions. Buffer solutions were prepared by dissolving the appropriate amount of formic acid, acetic acid, ammonium bicarbonate or boric acid in Milli-Q water, adjusting the pH to the desired value (pH 2.5, 5.0, 7.0, or 9.0, respectively) with 0.1 or 1M NaOH before completing the volume with water to get the desired buffer concentration. Finally, BGEs were prepared by dissolving the appropriate amount of the chiral selectors in the buffer solution. Stock standard solutions of racemic captopril, econazole and clenbuterol were prepared by dissolving the appropriate amount of these drugs in MeOH and razoxane was prepared by dissolving the appropriate amount in Milli-Q water/25% DMF (v/v). These solutions were stored at 4C. All solutions (buffers and standards) were filtered through 0.45mum pore size nylon membrane filters before their injection in the CE system., 21416-67-1

The synthetic route of 21416-67-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Quintana, Sara; Garcia, Maria Angeles; Marina, Maria Luisa; Gomez, Rafael; de la Mata, F. Javier; Ortega, Paula; Tetrahedron Asymmetry; vol. 28; 12; (2017); p. 1797 – 1802;,
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.163765-44-4,(R)-1-Boc-3-Methylpiperazine,as a common compound, the synthetic route is as follows.

Example 109a (R)-tert-Butyl 3-Methyl-4-(6-nitropyridin-3-yl)piperazine-1-carboxylate 109a A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and reflux condenser was charged with 1,4-dioxane (60 mL), 5-bromo-2-nitropyridine (2.0 g, 10.0 mmol), (R)-tert-butyl 3-methylpiperazine-1-carboxylate (2.0 g, 10.0 mmol), and cesium carbonate (6.5 g, 20 mmol). See . After bubbling nitrogen through the resulting mixture for 30 minutes, XantPhos (579 mg, 1.0 mmol) and tris(di-benzylideneacetone)dipalladium(0) (915 mg, 1.0 mmol) were added, and the reaction mixture was heated at 100 C. for 15 h. After this time the reaction was cooled to room temperature and filtered. The filtrate was partitioned between ethyl acetate (100 mL) and water (100 mL). The aqueous layer was separated and extracted with ethyl acetate (150 mL*3). The combined organic layer was washed with brine (50 mL) and dried over sodium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified on flash column eluting with 30:1 DCM/MeOH to afford 109a (1.6 g, 44%) as a yellow solid. MS: [M+H]+ 323. 1H NMR (500 MHz, DMSO) delta 8.21 (d, J=3.5, 1H), 8.18 (d, J=9.0, 1H), 7.43-7.45 (m, 1H), 4.33 (s, 1H), 3.92-3.99 (m, 1H), 3.80 (d, J=12.5, 2H), 3.06-3.23 (m, 3H), 1.43 (s, 9H), 1.09 (d, J=6.5, 3H).

163765-44-4, 163765-44-4 (R)-1-Boc-3-Methylpiperazine 2756811, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; GENENTECH, INC.; Crawford, James John; Young, Wendy B.; US2013/116245; (2013); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics