Heterocyclic Building Blocks-piperazine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.889958-14-9,1-Boc-2-oxopiperazine,as a common compound, the synthetic route is as follows.

EXAMPLE 25 t-Butyl 3-oxo-2-benzylidenyl-1-piperazinecarboxylate (25) To a solution of diisopropylamine (0.31 ml, 2.2 mmole) and dry THF (2 ml) at 0 C. under argon is added dropwise a hexane solution of n-butyllithium (0.90 ml, 2.2 mmole). After 1/2 hour, a solution of 2 (0.200 g, 1.00 mmole) in dry THF is added dropwise and stirred at 0 C. for 3 hours, and benzaldehyde (0.11 ml, 1.1 mmole) added dropwise. The reaction is stirred for 1 hour, the cooling bath is removed and the reaction stirred for an additional 2 hours. Acetyl chloride (0.078 ml, 1.1 mmole) was added and the mixture stirred overnight, quenched into ether/water, and purified as described in Example 23. Chromatography on silica gel with 10% methanol/chloroform yields colorless solid 25. M.p. 191-193 C.

889958-14-9, As the paragraph descriping shows that 889958-14-9 is playing an increasingly important role.

Reference£º
Patent; Richardson-Merrell Inc.; US4341698; (1982); 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.54699-92-2,4-Methyl-1-piperazineacetic acid,as a common compound, the synthetic route is as follows.

A solution of (1R,2R)-2-[[trans-2-[(1E,3E)-4-(4-cyano-2-fluorophenyl)-1,3-butadienyl]-1,3-dioxan-5-yl]thio]-1-(2,4-difluorophenyl)-1-[(1H-1,2,4-triazol-1-yl)methyl]propyl 2-(hydroxymethyl)benzoate (1.104 g, 1.63 mmol) obtained from Example 17-(4) in dichloromethane (25 ml) was cooled to 0C, and then 4-(N,N-dimethylamino)pyridine (299.1 mg, 2.45 mmol), 2-(4-methyl-1-piperazinyl)acetic acid (described in J. Med. Chem., 43, 1493 (2000); 387.3 mg, 2.45 mmol), and 1-ethyl-3-[3-(N,N-dimethylamino)propyl]carbodiimide (625.5 mg, 3.26 mmol) were added thereto. The reaction solution was stirred at room temperature for 4 hours, diluted with dichloromethane, and then the organic layer was washed successively with water and a saturated aqueous solution of sodium chloride. The solvent was evaporated under reduced pressure, and the residue was subjected to chromatography on a silica gel (40 g) column (eluent; ethyl acetate : methanol = 4 : 1) to give a mixture of the title target compound and 4-(N,N-dimethylamino)pyridine. The mixture was purified by recycle preparative HPLC [LC-908; Japan Analytical Industry Co., Ltd.; GPC column JAIGEL-1H (20 mm i.d. x 600 mm) and JAIGEL-2H (20 mm i.d. x 600 mm) connected in series for use; solvent, chloroform] to afford the title target compound (865.2 mg, 65% yield) as a colorless amorphous solid. NMR spectrum (400 MHz, CDCl3) delta ppm: 1.46 (3H, dd, J=7, 2 Hz), 2.29 (3H, s), 2.4-2.5 (4H, br s), 2.6-2.7 (4H, br s), 3.05 (1H, tt, J=12, 5 Hz), 3.31 (2H, s), 3.50 (1H, t, J=12 Hz), 3.53 (1H, t, J=12 Hz), 4.01 (1H, q, J=7 Hz), 4.12-4.21 (2H, m), 4 99 (1H, d, J=4 Hz), 5.45-5.55 (4H, m), 5.84 (1H, dd, J=15, 4 Hz), 6.57 (1H, dd, J=15, 10 Hz), 6.73 (1H, d, J=16 Hz), 6.93 (1H, dd, J=16, 10 Hz), 6.88-7.00 (2H, m), 7.34 (1H, dd, J=11, 1 Hz), 7.27-7.46 (3H, m), 7.53-7.60 (3H, m), 7.79 (1H, dd, J=8, 1 Hz), 7.90 (1H, s), 7.95 (1H, s) IR spectrum nu max KBr cm-1: 2230, 1726, 1503, 1275, 1257, 1051, 1140, 973 Mass spectrum m/z (FAB): 817 (M++1) Specific rotation [alpha]D25 +0.4 (c=0.99, CHCl3). A solution of (1R,2R)-2-[[trans-2-[(1E,3E)-4-(4-cyano-2-fluorophenyl)-1,3-butadienyl]-1,3-dioxan-5-yl]thio]-1-(2,4-difluorophenyl)-1-[(1H-1,2,4-triazol-1-yl)methyl]propyl 2-[[2-(4-methylpiperazin-1-yl)acetoxy]methyl]benzoate (280 mg, 0.343 mmol) obtained above in ethyl acetate (5 ml) was cooled to 0C, and hydrogen chloride (4N ethyl acetate solution; 95 mul, 0.38 mmol) was added thereto, and the mixture was stirred at 0C for 5 minutes. The solvent was evaporated under reduced pressure, and the residue was dried in vacuo to afford the mono hydrochloric acid salt of the title compound (298 mg, quantitative yield) as a pale yellow amorphous solid. NMR spectrum (400 MHz, CD3OD) delta ppm: 1.43 (3H, dd, J=7, 1 Hz), 2.87 (3H, s), 2.8-3.4 (8H, br), 3.04 (1H, tt, J=11, 5 Hz), 3.48 (1H, t, J=11 Hz), 3.53 (2H, s), 3.54 (1H, t, J=11 Hz), 4.06 (1H, q, J=7 Hz), 4.04-4.08 (2H, m), 4.17 (1H, ddd, J=11, 5, 2 Hz), 5.20 (1H, d, J=4 Hz), 5.46 (1H, d, J=14 Hz), 5.53 (1H, d, J=14 Hz), 5.58 (2H, s), 5.85 (1H, dd, J=15, 4 Hz), 6.57 (1H, dd, J=15, 10 Hz), 6.79 (1H, d, J=16 Hz), 7.01-7.11 (2H, m), 7.09 (1H, dd, J=16, 10 Hz), 7.46 (1H, td, J=8, 1 Hz), 7.50-7.61 (3H, m), 7.63 (1H, qd, J=7, 1 Hz), 7.78 (1H, t, J=8 Hz), 7.86 (1H, dd, J=7, 1 Hz), 7.95 (1H, s), 8.34 (1H, s) IR spectrum nu max KBr cm-1: 2230, 1726, 1503, 1274, 1257, 1140, 1050, 973 Mass spectrum m/z (FAB): 817 [M+(free base)+1] Specific rotation [alpha]D25 -1.9 (c=0.97, CHCl3). A solution of (1R,2R)-2-[[trans-2-[(1E,3E)-4-(4-cyano-2-fluorophenyl)-1,3-butadienyl]-1,3-dioxan-5-yl]thio]-1-(2,4-difluorophenyl)-1-[(1H-1,2,4-triazol-1-yl)methyl]propyl 2-[[2-(4-methylpiperazin-1-yl)acetoxy]methyl]benzoate (338.5 mg, 0.41 mmol) obtained above in ethyl acetate (5 ml) was cooled to 0C, and hydrogen chloride (4N ethyl acetate solution; 207 mul, 0.83 mmol) was added thereto, and the mixture was stirred at 0C for 5 minutes. The solvent was evaporated under reduced pressure, and the residue was dried in vacuo to afford the bis hydrochloric acid salt of the title compound (354 mg, quantitative yield) as a pale yellow amorphous solid. NMR spectrum (400 MHz, DMSO-d6) delta ppm: 1.35 (3H, dd, J=7, 2 Hz), 2.76 (3H, s), 2.82-2.92 (2H, br), 2.99 (1H, tt, J=11, 5 Hz), 3.06-3.16 (4H, br), 3.41 (2H, br d, J=15 Hz), 3.46 (1H, t, J=11 Hz), 3.47 (1H, t, J=11 Hz), 3.65 -3.75 (2H, br), 3.79 (1H, q, J=7 Hz), 3.96 (1H, ddd, J=11, 5, 2 Hz), 4.07 (1H, ddd, J=11, 5, 2 Hz), 5.05 (1H, d, J=5 Hz), 5.39 (1H, d, J=13 Hz), 5.40 (1H, d, J=14 Hz), 5.49 (1H, d, J=13 Hz), 5.56 (1H, d, J=14 Hz), 5.88 (1H, dd, J=15, 5 Hz), 6.56 (1H, dd, J=15, 11 Hz), 6.82 (1H, d, J=16 Hz), 7.16-7.20 (1H, m), 7.19 (1H, dd, J=16, 11 Hz), 7.31-7.37 (1H, m), 7.49-7.55 (1H, m), 7.55 (1H, td, J=9, 6 Hz), 7.60 (1H, d, J=7 Hz), 7.67-7.71 (2H, m), 7.84-7.89 (3H, m), 7.96 (1H, s), 8.44 (1H, s) Mass spectrum m/z (FAB): 817 [M+(free base)+1] Specific rotation [alpha]D25 -3.1 (c=1.87, CHCl3), 54699-92-2

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

Reference£º
Patent; Sankyo Company, Limited; EP1362856; (2003); 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

Intermediate 9: 3-(4-Methylpiperazin-1-yl)-propan-1-ol 1-Methylpiperazine (6.99 mL, 63 mol) was dissolved in toluene (30 mL). 3-Bromopropanol (2.62 mL, 30 mmol) was slowly and the mixture was stirred overnight at r.t. After heating to 80 C. for 2 h and cooling to r.t., the mixture was filtered and the filter cake was thoroughly washed with toluene. After removal of the solvent, the residue was subjected to distillation (b.p., 180 C./2 mbar) to obtain a colourless oil (4.08 g, 25.8 mmol, 86%). 1H NNR (CDCl3): delta=1.70 (Psi-quint, J?5.8 Hz, 2 H), 2.26 (s, 3 H), 2.35-2.6 (m, 8 H), 2.60 (Psi-t, J=5.8 Hz, 2 H), 3.77 (Psi-t, J=5.3 Hz, 2 H), 4.09 (s, br., 1 H)., 109-01-3

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

Reference£º
Patent; 4SC AG; US2006/142570; (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

4-chloro-3-(3,4-difluorophenyl)-1-[2-(4-methylpiperazin-1-yl)ethyl]-5-phenyl-pyrazolo[3,4-c]pyridazine (Compound 10) A mixture of 4-chloro-3-(3,4-difluorophenyl)-5-phenyl-1H-pyrazolo[3,4-c]pyridazine (0.33 mmol), 2-(4-methylpiperazin-1-yl)ethanol (0.65 mmol), diethyl azodicarboxylate (114 mg, 0.65 mmol) and triphenyl phosphine (171 mg, 0.65 mmol) in 1,4-dioxane (2 mL) was heated using microwave irradiation to a temperature between 85 and 120¡ã C. for a 30 to 90 min period. The reaction mixture was concentrated in vacuo and the residue was purified by preparative HPLC to provide Compound 10. 1H NMR delta (ppm)(CHCl3-d): 7.78-7.75 (2H, m), 7.65-7.59 (1H, m), 7.58-7.51 (4H, m), 7.33-7.29 (1H, m), 4.93 (2H, t), 3.16 (2H, t), 3.08 (4H, bs), 1.59 (4H, bs), 2.67 (3H, s). LCMS (10 cm_ESCI_Bicarb_MeCN) Rt 4.27 min; m/z 469 [M+H] 96.02percent purity., 5464-12-0

Big data shows that 5464-12-0 is playing an increasingly important role.

Reference£º
Patent; Usher III Initiative; Buerli, Roland Werner; Krishna Esmieu, William Rameshchandra; Lock, Christopher James; Malagu, Karine Fabienne; Owens, Andrew Pate; Harte, William E.; US2014/121205; (2014); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

59702-07-7, 1-Methylpiperazin-2-one is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

59702-07-7, A solution of 2,6-dichloro-4-cyclopropylpyridine-3,5-dicarbonitrile (synthesis described in example 4 step 2, 238 mg, 1 mmol) 1-methylpiperazin-2-one (114 mg, 1 mmol), and triethylamine (121 mg, 1.2 mmol) in N,N-dimethylformamide (8 mL) was stirred at room temperature for 30 minutes, then diluted with water (50 mL) and extracted with ethyl acetate (50 mL x 2). The combined organic layers were dried and concentrated under vacuum to give 2-chloro-4-cyclopropyl-6-(4-methyl-3-oxopiperazin-1-yl)pyridine-3,5-dicarbonitrile (260 mg, 83percent) as a brown solid. LCMS m/z = 315.8 [M+H]+.

As the paragraph descriping shows that 59702-07-7 is playing an increasingly important role.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Nicholas David; BENOWITZ, Andrew B.; RUEDA BENEDE, Maria Lourdes; EVANS, Karen Anderson; FOSBENNER, David T.; KING, Bryan Wayne; LI, Mei; MILLER, William Henry; REIF, Alexander Joseph; ROMERIL, Stuart Paul; SCHMIDT, Stanley J.; WIGGALL, Kenneth; (1283 pag.)WO2017/216726; (2017); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

78818-15-2,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.78818-15-2,Benzyl 3-oxopiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

Reference Example 17 4-Benzyloxycarbonyl-1-[4-(tert-butoxycarbonylamino)benzyl]-2-piperazinone According to a similar method described in Reference Example 2, the title compound of pale yellow amorphous was obtained from 4-benzyloxycarbonyl-2-piperazinone and 4-(tert-butoxycarbonylamino)benzylbromide. 1H-NMR (CDCl3) delta: 1.51 (9H, s), 3.23 (2H, t, J=5.2 Hz), 3.63 (2H, t, J=5.3 Hz), 4.22 (2H, s), 4.55 (2H, s), 5.15 (2H, s), 7.10-7.40 (10H, m). IR (KBr): 1707, 1655, 1530, 1235, 1163 cm-1.

As the paragraph descriping shows that 78818-15-2 is playing an increasingly important role.

Reference£º
Patent; Takeda Chemical Industries, Ltd.; US6403595; (2002); 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.196811-66-2,tert-Butyl 4-carbamothioylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

To a suspension of 4-thiocarbamoyl-piperazine-1-carboxylic acid tert-butyl ester (13.3 mmol) in ethanol (60 mi) was added 4- (2-bromoacetyl)-benzoic acid (13.3 mmol) and 4- methylmorpholine (13.9 mmol). The reaction was heated at reflux for 2. 5 h. The reaction was concentrated in vacuo and the solid washed with water (200 ml) to yield the title compound as a white solid (3.9 g). 1H NMR (400MHz, CDCI3) 1.45 (9H, s), 3.58 (8H, m), 4.86 (1H, s), 6.95 (1H, s), 7.97 (2H, d, J 8 Hz), 8.1 (2H, d, J8Hz).

196811-66-2, The synthetic route of 196811-66-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MEDIVIR AB; WO2005/66180; (2005); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

17766-28-8, 1-Cyclohexylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

About 17.3kg of 4-((3-bromo-6-oxo-6H-anthra[l,9-cd]isoxazol-5- yl)amino)benzoic acid was mixed with about 238L of DMSO. About 11L of TEA and 12kg of 1-cyclohexyl piperazine were added to the reaction. Temperature was then raised to about 60- 65C. After 2-3 hours, slowly added about 116L of MTBE and MeOH (10: 1) solution and adjusted the temperature to 40-50C. The solid was centrifuged and washed by 22.5L of MTBE and MeOH (10: 1) solution and followed by about 22L of MeOH. Solid was dried under reduced pressure at about 25-30C for 12-24 hours. About 1.8kg phosphoric acid was dissolved in 90L of N-methyl pyrrolidone (NMP). Previously obtained crude product was dissolved in about 163L of NMP. Under about 40C, two solutions were mixed together for 1-2 hours. Then about 5.5kg of ECOSORB C-941 in about 20L of NMP was added to the previously mixed solution. The mixture was stirred for another 2- 3 hours under nitrogen protection before filtration. About 600L of purified water was slowly added to the solution under about 40C. Solid was centrifuged and washed with about 21L of water and followed by about 56L of MTBE. Solid was dried under reduced pressure at about 25- 30C for 8-12 hours to obtain the 4-((3 -(4-cyclohexylpiperazin- l-yl)-6-oxo-6H-anthra[ 1,9- cd]isoxazol-5-yl)amino)benzoic acid at about 98% purity and about 91% yield.

17766-28-8, As the paragraph descriping shows that 17766-28-8 is playing an increasingly important role.

Reference£º
Patent; PURDUE PHARMA L.P.; WU, Jay Jie-Qiang; WANG, Ling; (31 pag.)WO2017/27465; (2017); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

55276-43-2, 1-Methanesulfonylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde (II) (1.00 g), 1-methanesulfonyl-piperazine (750 mg) and trimethylorthoformate (3.80 mL) was stirred in 1,2-dichloroethane (30 mL) for 6 hrs at room temperature. To this was added sodium triacetoxyborohydride (900 mg) and the reaction mixture was stirred for 24 hours at room temperature. The mixture was then quenched with brine, extracted with dichloromethane, dried (MgSO4) and the solvent removed in vacuo. The residue was triturated with hot ethyl acetate to yield the title compound (VI) as a white solid (1.01 g)., 55276-43-2

The synthetic route of 55276-43-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PIRAMED LIMITED; US2008/76768; (2008); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

934-98-5, 2-(4-Methylpiperazin-1-yl)ethanamine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

934-98-5, General procedure: At room temperature, to a red solution of compound 2 (150 mg,0.5 mmol) and triethylamine (0.14 mL, 1.0 mmol) in chloroform(40 mL), thionyl chloride (2.5 mL) was added dropwise. Themixture was stirred and heated under reflux for 5 h. The mixturegradually became a red solution. The reaction solution was then cooled to room temperature. The solvent was evaporated underreduced pressure. The residue was obtained under reduced pressurefor a period to get rid of most of the residual SOCl2 to give an orange solid residue. 4-(Dimethylamino)pyridine (70 mg,0.6 mmol) and different amine or alcohol derivative (1.80 mmol) inchloroform (30 mL) were added dropwise to the resultant residue.The reaction mixture instantaneously became a red solution. Thereaction mixture was heated under reflux for 5 h, and cooled toroom temperature. The solvent was evaporated under reducedpressure. The crude product was purified by silica gel columnchromatography to give the target compound.

934-98-5 2-(4-Methylpiperazin-1-yl)ethanamine 70284, apiperazines compound, is more and more widely used in various fields.

Reference£º
Article; Yu, Le-Mao; Zhang, Xiao-Ru; Li, Xiao-Bing; Yang, Yuan; Wei, Hong-Yu; He, Xi-Xin; Gu, Lian-Quan; Huang, Zhi-Shu; Pommier, Yves; An, Lin-Kun; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 525 – 533;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics