Heterocyclic Building Blocks-piperazine

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

EXAMPLE 24A 3-methyl-1-pyridin-2-ylpiperazine hydrobromide 2-Methylpiperazine (1.0 g, 0.01 mol, racemic mixture) and 2-bromopyridine (10 mL, 0.1 mol) were combined and heated at 120 C. for 16 hours. The reaction mixture was cooled to 23 C. and partitioned between ethyl acetate and water. The layers were separated, and the water layer was concentrated under reduced pressure. The residue was triturated with ethyl acetate, dichloromethane, and methanol to afford 460 mg (26% yield) of the title compound as an off-white solid. 1H NMR (300 MHz, DMSO-d6) delta1.27 (d, J=6.6 Hz, 3H), 2.90 (dd, J=10.5, 14.1 Hz, 1H), 3.10 (m, 2H), 3.40 (m, 2H), 4.32 (m, 2H), 6.77 (dd, J=4.8, 6.9 Hz, 1H), 6.98 (d, J=8.1 Hz, 1H), 7.64 (m, 1H), 8.15 (m, 1H), 8.63 (bs, 1H), 8.92 (bs, 1H); MS (APCI) m/e 178 (M+H)+.

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

Reference£º
Patent; Cowart, Marlon D.; Bhatia, Pramila A.; Daanen, Jerome F.; Stewart, Andrew O.; Patel, Meena V.; Kolasa, Teodozyj; Brioni, Jorge D.; Rohde, Jeffrey; US2002/169167; (2002); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.314741-40-7,(S)-tert-Butyl 3-(hydroxymethyl)piperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

5-(oxiran-2-yl)-2-benzofuran-1(3H)-one (1.5 g, 8.5 mmol) and commercially available (S)-4-N-BOC-2-hydroxymethyl piperazine (2.394 g, 11.07 mmol) were combined in ethanol (10 mL) in a microwave tube. The mixturewas degassed then heated for 60 min at 150 C. LC-MS showed the product peak. The reaction was worked up byadding ethyl acetate and washing once with brine. The organic layer was separated, dried, and concentrated todryness. The crude product was purified by MPLC using an 80g Redi-sep column and eluted with 50%-100% EtOAc/hexane yielding the title compound., 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; Merck Sharp & Dohme Corp.; PASTERNAK, Alexander; BLIZZARD, Timothy; CHOBANIAN, Harry; DE JESUS, Reynalda; DING, Fa-Xiang; DONG, Shuzhi; GUDE, Candido; KIM, Dooseop; TANG, Haifeng; WALSH, Shawn; PIO, Barbara; JIANG, Jinlong; (128 pag.)EP2744499; (2016); B1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.74879-18-8,(S)-(+)-2-Methylpiperazine,as a common compound, the synthetic route is as follows.

Example 68 (3S)-1-{[6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]methyl}-3-methylpiperazine To a solution of 6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridine-3-carbaldehyde (250 mg) in tetrahydrofuran (10 mL) was added (2S)-2-methylpiperazine (270 mg), and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added sodium triacetoxyborohydride (230 mg), and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to preparative HPLC to give the title compound (111 mg, yield 38%) as a colorless amorphous solid. MS:549(MH+). 1H NMR (300 MHz, CDCl3) 50.98 – 1.03 (2 H, m), 1.05 (3 H, d, J=6.2 Hz), 1.29 – 1.49 (5 H, m), 1.52 – 1.70 (3 H, m), 1.82 – 1.97 (2 H, m), 2.05 – 2.15 (2 H, m), 2.36 – 2.49 (1 H, m), 2.66 – 2.79 (2 H, m), 2.81 – 3.05 (3 H, m), 3.19 – 3.36 (2 H, m), 3.40 – 3.50 (2 H, m), 3.84 – 4.00 (2 H, m), 4.12 – 4.23 (1 H, m), 6.15 (1 H, t, J=3.0 Hz), 6.63 (1 H, dd, J=2.4, 3.5 Hz), 7.40 (2 H, d, J=8.3 Hz), 7.44 – 7.50 (1 H, m), 7.52 – 7.63 (1 H, m), 7.75 – 7.88 (2 H, m), 8.29 (1 H, d, J=1.5 Hz), 9.22 (1 H, brs)., 74879-18-8

As the paragraph descriping shows that 74879-18-8 is playing an increasingly important role.

Reference£º
Patent; Takeda Pharmaceutical Company Limited; EP2149550; (2010); A1;,
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122323-88-0, Methyl piperazine-2-carboxylate dihydrochloride is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

REFERENCE EXAMPLE 16 A solution of di-tert-butyl dicarbonate (5.0 g) in dichloromethane (30 ml) is added dropwise, taking one hour at 0 C. while stirring, to a mixture of methyl piperazine-2-carboxylate dihydrochloride (5.0 g), triethylamine (7 g) and dichloromethane (70 ml). The reaction mixture is poured into ice-water and extracted with dichloromethane. The organic layer is washed with water and dried, then the solvent is distilled off under reduced pressure. The residue is purified by means of a silica gel column chromatography (eluent, dichloromethane:acetone:ethanol =5:5:1) to afford methyl 4-tert-butoxycarbonylpiperazine-2-carboxylate as a colorless oily product (4.9 g)., 122323-88-0

As the paragraph descriping shows that 122323-88-0 is playing an increasingly important role.

Reference£º
Patent; Takeda Chemical Industries, Ltd.; US4997836; (1991); A;,
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196811-66-2, tert-Butyl 4-carbamothioylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of tert-butyl 4-carbamothioyl pi perazi ne-I -carboxyl ate (synthesized according to Example 5, Step 1, 1.31 g, 5.36 mmol) in isopropanol (15 mL), tert-butyl 3- bromo-2,4-dioxopiperidine-I-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 desiredproduct was extracted with diethyl ether (2 x 30 mL), dried over Na2504 and concentrated, affording the title product. Yield: 74% (1.42 g, yellow solid). LCMS: (Method A) 239.0 (MBoc+H), Rt. 0.70 mm, 48.39% (Max)., 196811-66-2

196811-66-2 tert-Butyl 4-carbamothioylpiperazine-1-carboxylate 12093220, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut, Gajendra; (280 pag.)WO2017/144633; (2017); A1;,
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55121-99-8, (4-Aminophenyl)(4-methylpiperazin-1-yl)methanone is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,55121-99-8

mCPBA (<77% pure) (77 mg, assumed 0.342 mmol) in DCM (0.5 mL) was added to a stirred solution of 6- (2,6- dichlorophenyl ) -2 - (methylthio) pyrido [4 , 3 -d] pyrimidin-5 ( 6H) one (100 mg, 0.296 mmol) in toluene (3.0 mL) at RT under nitrogen. After 30 min, DIPEA (0.155 mL, 0.887 mmol) and (4 -aminophenyl ) (4 -methylpiperazin- 1 -yl ) methanone (64.8 mg, 0.296 mmol) [commercially available] were added,successively and the temperature was increased to 60 C. After 16 h, the reaction mixture was cooled and loaded directly onto a KP-NH column and purified by flash chromatography (0-100%, EtOAc in cyclohexane) . The resultant material required re-purification by flash chromatography on a KP-Sil column (0-10%, MeOH in EtOAc) . The resultant material required re-purification by preparative HPLC . The pure fractions were concentrated and the resultant material was freeze-dried to give the title compound (10.2 mg, 7%) as a white solid. LCMS (Method A): RT = 0.79 min, m/z = 509, 511 [M+H]+. 1U NMR (500 MHz, methanol -d4 ) : delta 9.28 (s, 1H) , 7.98 (d, 2H) , 7.66-7.62 (m, 2H) , 7.56-7.51 (m, 2H) , 7.48-7.43 (m, 2H) , 6.69 (d, 1H) , 3.68 (br s, 4H) , 2.49 (br s, 4H) , 2.34 (s, 3H) . 55121-99-8 (4-Aminophenyl)(4-methylpiperazin-1-yl)methanone 231408, apiperazines compound, is more and more widely used in various fields. Reference£º
Patent; ALMAC DISCOVERY LIMITED; O’DOWD, Colin Roderick; ROUNTREE, James Samuel Shane; BURKAMP, Frank; WILKINSON, Andrew John; WO2014/167347; (2014); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.120737-59-9,tert-Butyl 3-methylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.,120737-59-9

Step 1 – Synthesis of 3-methyl-4-(2-nitro-phenyl)-piperazine-carboxylic acid tert- butyl ester 1 -Bromo-2-nitrobenzene (2.00 mmol, 404 mg), Pd(OAc)2 (0.100 mmol, 22.5 mg), Palucki-Phos (0.120 mmol, 45.8 mg) and Cs2CO3 (3 mmol, 1 g) were loaded into a Schlenk tube containing a stir bar. The tube was capped with a rubber septum, evacuated and refilled with nitrogen. 3-Methyl-piperazine-1 -carboxylic acid te/f-butyl ester (0.48 ml_, 2.5 mmol) and toluene (3 ml_) were added to the reaction through the septum via syringe and the tube was sealed with a Teflon screw cap under a flow of nitrogen, and put into an oil bath at 100 0C. The reaction was allowed to stir at this temperature for about 15 hours and was then was cooled to room temperature and filtered through celite. The filtrate was concentrated in vacuo and the resulting residue was purified using flash column chromatography on silica gel (eluent: Hexane/EtOAc (5:1) to provide 3-methyl-4-(2-nitro-phenyl)-piperazine- carboxylic acid tert-butyl ester.

As the paragraph descriping shows that 120737-59-9 is playing an increasingly important role.

Reference£º
Patent; SCHERING CORPORATION; WO2008/54702; (2008); A1;,
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216144-45-5, 4-(4-Methylpiperazin-1-yl)benzylamine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The solution of compound 5 (150 mg, 0.58 mmol), 4-(4-Methylpiperazino)benzylamine (118 mg, 0.58 mmol) and DIPEA (0.15 ml, 0.86 mmol) DMSO (3.5 mL) was stirred at 105 C. for 2 hours. TLC was checked and the starting material was consumed. The reaction mixture was added to half-saturated ammonium chloride in water (80 mL) and stirred for 30 min, then cooled with ice bath. The solids were collected by filtration, washed by water. The crude product was purified by column chromatography (0-10% MeOH in DCM) to give the product compound 29 as yellow solids. (98 mg, 39% yield). 1H NMR (400 MHz, DMSO-d6) delta 12.10 (br, 1H), 10.67 (s, 1H), 8.34 (s, 1H), 8.28 (s, 1H), 7.20 (d, J=8.8 Hz, 2H), 6.90 (d, J=8.8 Hz, 2H), 5.69 (s, 1H), 4.67 (d, J=5.6 Hz, 2H), 3.10 (m, 4H), 2.43 (m, 4H), 2.21 (s, 3H), 1.98 (m, 1H), 0.98 (m, 2H), 0.79 (m, 2H); ESI-MS: calcd for (C23H27N9) 429, found 452 (MNa+).

216144-45-5, 216144-45-5 4-(4-Methylpiperazin-1-yl)benzylamine 2776493, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; NantBio, Inc.; Tao, Chunlin; Wang, Qinwei; Asad, Sharif; Weingarten, Paul; Ci, Sherry; US2018/346450; (2018); A1;,
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13754-38-6, 1-Benzoylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

13754-38-6, General procedure: To a mixture of 1-benzoylpiperazine (1.0 eq) and potassium carbonate (2.0 eq) in dimethylformamide was added dropwise a solution of the corresponding substituted 9-bromo-9H-fluorene (1.0 eq) in dimethylformamide (The synthesis of 9-bromo-9H-fluorene derivatives is reported in supporting information). After stirring for 24 h at room temperature, solvent was removed and the crude residue was dissolved in diethyl ether, washed with brine, dried over magnesium sulfate,filtered and concentrated under vacuum. The residue was purified by flash chromatography as indicated in each case to afford the title compound. Reagents: 1-Benzoylpiperazine (0.08 mmol, 15 mg), potassium carbonate (0.15 mmol, 20 mg) and 9-bromo-3-hexyl-9H-fluorene (0.08 mmol, 25 mg). The crude product was purified by flash chromatography (isocratic, petroleum ether/ethyl acetate 70/30 in 15 min) to afford a yellow oil (18 mg, 56%). TLC Rf: 0.11 (petroleum ether/ethyl acetate 80/20). IR (cm-1): 630, 674, 697, 708, 739, 768, 787, 1001, 1015, 1142, 1155, 1255, 1277, 1301, 1424, 1447, 1633, 2854, 2925. HPLC: method 2, rt = 2.56 min, purity 97%. 1H NMR (300 MHz, CDCl3) delta (ppm): 0.85-1.00 (m, 3H); 1.29-1.48 (m, 6H); 1.62-1.77 (m, 2H); 2.46 (s, 2H); 2.72 (t, J = 7.5 Hz, 2H); 2.86 (s, 2H); 3.38 (s, 2H); 3.82 (s, 2H); 4.87 (s, 1H); 7.15 (dd, J = 1.5 Hz, 7.5 Hz, 1H); 7.32 (td, J = 1.5 Hz, 7.5 Hz, 1H); 7.35-7.48 (m, 6H); 7.53 (s, 1H); 7.55 (d, J = 5.4 Hz, 1H), 7.64 (d, J = 7.5 Hz, 1H); 7.70 (d, J = 7.5 Hz, 1H). 13C NMR (75 MHz, CDCl3) delta (ppm): 14.1 (CH3); 22.6 (CH2); 29.1 (CH2); 31.7 (CH2); 31.8 (CH2); 36.1 (CH2); 43.0 (CH2); 48.4 (CH2); 48.8 (CH2); 49.5 (CH2); 69.7 (CH); 119.7 (CH); 119.8 (CH); 125.6 (CH); 125.9 (CH); 127.0 (CH); 127.1 (2 * CH); 127.5 (CH); 128.2 (CH); 128.4 (2 * CH); 129.6 (CH); 135.9 (C); 140.7 (C); 141.1 (C); 141.2 (C); 143.3 (C); 143.8 (C); 170.3 (C). MS (DCI/CH4) m/z: 438.26 [M+H+], 249.16 [M-188]. HRMS (DCI/CH4): for C30H34N2O [M+H+]: calcd: 438.2671; found: 438.2674.

As the paragraph descriping shows that 13754-38-6 is playing an increasingly important role.

Reference£º
Article; Chollet, Aurelien; Mori, Giorgia; Menendez, Christophe; Rodriguez, Frederic; Fabing, Isabelle; Pasca, Maria Rosalia; Madacki, Jan; Kordulakova, Jana; Constant, Patricia; Quemard, Annaik; Bernardes-Genisson, Vania; Lherbet, Christian; Baltas, Michel; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 218 – 235;,
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75336-86-6,75336-86-6, (R)-2-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(R)-2-methylpiperazine (5.025 g, 50.2 mmol) was dissolved in DCM (100 mL). A solution of boc anhydride (5.47 g, 25.1 mmol) in DCM (50 mL) was added dropwise at 0 C. The reaction mixture was stirred at rt for 1 h. The solution was filtered and concentrated under reduced pressure. Water (100 mL) was added to the residue, which was filtered again. The filtrate was saturated with K2CO3 and extracted with Et2O (3¡Á150 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to provide 5.04 g title compound (50%) as a solid. 1H NMR (300 MHz, CDCl3) delta ppm 1.03 (d, J=6.3 Hz, 3H) 1.45 (s, 9H) 1.56 (s, 1H) 2.30-2.46 (m, 1H) 2.65-2.72 (m, 1H) 2.74-2.76 (m, 2H) 2.93-2.95 (m, 1H) 3.93 (br s, 2H).

The synthetic route of 75336-86-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ASTRAZENECA AB; US2010/216812; (2010); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics