Category: 5464-12-0

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5464-12-0,1-(2-Hydroxyethyl)-4-methylpiperazine,as a common compound, the synthetic route is as follows.

300 mg mixture of 2,6-dichloro-4- [4-chloro-6-(4-fluorophenyl)thieno [2,3 -d]pyrimidin-5 -yl] -3,5 -dimethyl-pheno 1 and 4- [4-bromo-6-(4-fluorophenyl)thieno [2,3 -d]pyrimidin-5 -yl] -2,6-dichloro-3 ,5 -dimethyl-pheno 1 (0.62 mmo 1), 286 mg 2-(4-methylpiperazin- 1 -yl)ethano 1(1.98 mmol) and 520 mg triphenyl phosphine (1.98 mmol) were dissolved in 10 mL drytoluene, then 460 mg ditertbutyl azodicarboxylate (1.98 mmol) was added. The mixturewas stirred at 50 ¡ãC under nitrogen until no further conversion was observed. The volatiles were evaporated under reduced pressure and the crude intermediate was purified via flash chromatography using EtOAc and methanol as eluents to obtain 4-chloro-5-[3,5-dichloro- 2,6-dimethyl-4- [2-(4-methylpiperazin- 1 -yl)ethoxy]phenyl] -6-(4-fluorophenyl)thieno [2,3 -d]pyrimidine and 4-bromo-5 -[3 ,5-dichloro-2,6-dimethyl-4- [2-(4-methylpiperazin- 1-yl)ethoxy]phenyl]-6-(4-fluorophenyl)thieno[2,3-d]pyrimidine as a 35:65 mixture of products.

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

Reference£º
Patent; LES LABORATOIRES SERVIER; VERNALIS (R&D) LIMITED; SZLAVIK, Zoltan; SZABO, Zoltan; CSEKEI, Marton; PACZAL, Attila; KOTSCHY, Andras; BRUNO, Alain; GENESTE, Olivier; CHEN, I-Jen; DAVIDSON, James Edward Paul; MURRAY, James Brooke; ONDI, Levente; RADICS, Gabor; SIPOS, Szabolcs; PROSZENYAK, Agnes; PERRON-SIERRA, Francoise; BALINT, Balazs; (188 pag.)WO2016/207226; (2016); 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.5464-12-0,1-(2-Hydroxyethyl)-4-methylpiperazine,as a common compound, the synthetic route is as follows.,5464-12-0

Example 43 2-(4-Methylpiperazin-1-yl)ethyl 4-(4-chlorobenzyl)piperazine-1-carboxylate 2-(4-Methyl-piperazin-1-yl)-ethanol (0.86 g, 6 mmol) and NMM (0.58 mL, 6 mmol) were dissolved in DCM (8 mL) and the reaction mixture was cooled to 0¡ã C. 4-Nitrophenyl chloroformate (1.29 g, 6 mmol) was added and stirred for 1 h. To the reaction mixture was added a solution of 1-(4-chloro-benzyl)-piperazine (1.05 g, 5 mmol) and DIPEA (6.0 mL, excess) in DMF (20 mL). The reaction mixture was stirred at room temperature overnight and then concentrated in vacuo. The residue was dissolved in EtOAc (150 mL), washed with sat aq Na2CO3 solution (6*100 mL), dried (MgSO4) and dried in vacuo. The residue was initially purified by column chromatography (normal phase, 20 g, Strata SI-1, silica gigatube, 20 mL/min, gradient 0percent to 15percent MeOH in DCM) and then further purified by reverse phase column chromatography (LiChroprep RP-18, 40-63 mum, 460*26 mm (100 g), 30 mL/min, gradient 0percent to 30percent (over 40 min) MeOH in water with 1percent formic acid). The residue was stirred for 2 h in DCM (10 mL) with K2CO3 (~0.20 g), filtered and then dried in a vacuum oven overnight to give 2-(4-methylpiperazin-1-yl)ethyl 4-(4-chlorobenzyl)piperazine-1-carboxylate (0.51 g, 28percent) as a pale yellow oil. Analytical HPLC: purity 99.7percent (System A, RT=3.39 min); Analytical LCMS: purity 100percent (System A, RT=3.83 min), ES+: 381.5 [MH]; HRMS calcd for C19H29ClN4O2: 380.1979, found 380.1996.

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

Reference£º
Patent; Biovitrum AB; US2009/281087; (2009); 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.5464-12-0,1-(2-Hydroxyethyl)-4-methylpiperazine,as a common compound, the synthetic route is as follows.

To a solution of Intermediate 13b (1.15 g, 5.0 mmol), 2-(4-methyl- piperazin-l -yl)-ethanol (864 mg, 6.0 mmol) and triphenylphosphine (2.62 g, 10.0 mmol) in THF (10 mL) was added diisopropyl azodicarboxylate (2.0 g, 10.0 mmol) dropwise and stirred for 75 min. The mixture was diluted with diethyl ether (50 mL) and extracted with 10percent aqueous citric acid soln (2 x). The combined aqueous layers were basified with solid potassium carbonate until pH = 9. The aqueous layer was then extracted with ethyl acetate (3 x). The combined ethyl acetate layers were washed with brine, dried (NaSO4) and evaporated in vacuo. Purification by FCC using 0- 12percent [9: 1 MeOH/880 ammonia] in DCM. The resulting product was crystallised (diethyl ether) to give the title compound (270 mg, 0.756 mmol, 15percent). LCMS (Method 1): Rt 2.31 , 1.72 min, m/z 358/359 [MH+].

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

Reference£º
Patent; CHIESI FARMACEUTICI S.P.A.; VAN NIEL, Monique Bodil; RAY, Nicholas Charles; ALCARAZ, Lilian; PANCHAL, Terry Aaron; JENNINGS, Andrew Stephen Robert; ARMANI, Elisabetta; CRIDLAND, Andrew Peter; HURLEY, Cristopher; WO2013/83606; (2013); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

5464-12-0,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5464-12-0,1-(2-Hydroxyethyl)-4-methylpiperazine,as a common compound, the synthetic route is as follows.

EXAMPLE 22: 2-Chloro-6-(2-(4-methylpiperazin- 1 -yl)methoxy)pyridine31To a suspension of 2-(4-methylpiperazine-l-yl)ethanol (50mg, 0.347mmol) in dioxane (3ml) at 0¡ãC, KOlBu (50mg, 0.347mmol) was added and the reaction mixture was stirred for lOmin. Ice bath was removed and the reaction mixture was allowed to attain room temperature. The mixture was again cooled to 0¡ãC and 2, 6-Dichloropyrazine (200mg, 1.04mmol) was added. Reaction mixture was allowed to stir at RT for 24h after which it was concentrated and was purified by flash column chromatography over 230-400 silica gel using 5-8percent MeOH/DCM system to afford the desired product 31, 30mg (Yield:35 percent) as brown gummy liquid. The product was confirmed by 1HNMR (not clean but characteristic peaks were present); MS: 256, (M+l), LCMS -90percent.

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

Reference£º
Patent; ARRIEN PHARMAEUTICALS LLC; VANKAYALAPATI, Hariprasad; APPALANENI, Rajendra, P.; REDDY, Y., Venkata Krishna; WO2012/135631; (2012); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

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

To a solution of the acid of example 1 (20 mg, 0.015 mmol), triethylamine (6.3 DL, 0.045 mmol), and 4-dimethylaminopyridine (catalytic amount) in dichloromethane (1 mL) was isopropenylchloroformate (5DL, 0.045 mmol) at room temperature. After 5 minutes, l-(2- hydroxyethyl)-4-methylpiperazine (43 mg, 0.15 mmol) was added. The reaction mixture was stirred at room temperature for 3 hours. The solvent was evaporated, and the residue was purified on preparative reversed-phase HPLC. The product was obtained as a light yellow solid after lyophilization. 1H NMR (CD3OD5 500MHz): d 8.61 (d, J=9.5, 1 H), 8.57 (m, 2 H)3 8.43 (s, 1 H), 8.18 (S5 1 H)5 8.14 (d5 J=Il. OHz, 1 H), 7.87 (m, 1 H)5 7.82 (m, 1 H), 7.42 (t, J=7.8Hz, 1 H)5 7.22 (d, J=7.0 Hz, 1 H), 6.19 (d, J=12.5 Hz, 1 H), 5.90 (m, 1 H)5 5.78 (dd, J=10.5 Hz, 4.5 Hz5 1 H), 5.39 (m5 1 H)5 5.21 (s, 1 H), 5.06 (d, J=12.5 Hz, IH), 4.96 (d, J=10.5Hz, 1 H), 4.57 (m, 3 H), 4.41 (d, J=9.5 Hz, 1 H), 4.37 (m5 1 H), 4.30 (d, 10.5 Hz, 1 H), 4.06 (m, 1 H), 3.95 (s, 3 H), 3.20 (s, 2 H)5 3.02 (s, 6 H), 2.96 (m5 2 H)5 2.89 (s, 3 H), 2.80 (m, 1 H)5 2.17 (m, 2 H), 2.05 (s, 3 H), 1.75 (s, 3 H), 1.40 (d, J=6 Hz5 3 H)5 0.99 (d, J=7.5 Hz5 3 H).

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

Reference£º
Patent; MERCK & CO., INC.; WO2007/127135; (2007); A2;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

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

Sodium hydride, 60percent dispersion in mineral oil (252 mg, 6.29 mmol) was added, portionwise, to an ice-cooled solution of 2-(4-methyl-piperazin-l-yl)-ethanol (863 mg, 5.99 mmol) and 2-chloro-5- nitropyridine (1.0 g, 6.29 mmol) in DMF (20 ml). The ice-cooling was removed after 1 hour and the mixture was allowed to stir at rt overnight. The reaction mixture was added to ice/water and subsequently extracted with EtOAc (x2). The combined organic extracts were washed with water (x4) and brine (xl), dried and concentrated. The crude product was purified by flash column chromatography on silica gel (60 g) eluting with 10:1 DCM:MeOH to give the product as a brown oil (400 mg, 24percent). 1H NMR (400 MHz, DMSO-^6) delta ppm 2.13 (s, 3 H), 2.21 – 2.54 (m, 8 H), 2.70 (t, /=5.95 Hz, 2 H), 4.50 (t, J=5.95 Hz, 2 H), 7.04 (d, .7=9.16 Hz, 1 H), 8.47 (dd, 7=9.16, 2.75 Hz, 1 H), 9.07 (d, 7=2.29 Hz, 1 H); m/z (ES+APCI)+: 267 [M+H]+.

As the paragraph descriping shows that 5464-12-0 is playing an increasingly important role.

Reference£º
Patent; MEDICAL RESEARCH COUNCIL; WO2009/122180; (2009); 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.5464-12-0,1-(2-Hydroxyethyl)-4-methylpiperazine,as a common compound, the synthetic route is as follows.

10.373 g (50 mmol) 4-bromo-2-chlorophenol, 14.442 g 2-(4-methylpiperazin-1-yl)ethanol(100 mmol) and 26.229 g PPh3 (100 mmol) were dissolved in 250 mL toluene, then 23 .027g diter/butyl azodicarboxylate (100 nimol) was added. The mixture was stirred at 50¡ãCunder N2 until no further conversion was observed. The toluene was evaporated under reduced pressure and the residue was purified via flash chromatography using EtOAc and MeOll as eluentsMS (M+H)t 333.0., 5464-12-0

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

Reference£º
Patent; LES LABORATOIRES SERVIER; VERNALIS (R&D) LIMITED; KOTSCHY, Andras; SZLAVIK, Zoltan; CSEKEI, Marton; PACZAL, Attila; SZABO, Zoltan; SIPOS, Szabolcs; RADICS, Gabor; PROSZENYAK, Agnes; BALINT, Balazs; BRUNO, Alain; GENESTE, Olivier; DAVIDSON, James Edward Paul; MURRAY, James Brooke; CHEN, I-Jen; PERRON-SIERRA, Francoise; WO2015/97123; (2015); 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.5464-12-0,1-(2-Hydroxyethyl)-4-methylpiperazine,as a common compound, the synthetic route is as follows.

General procedure: 1) (Cyanomethylene)tributylphosphorane (262 muL, 1.00 mmol) was added to a solution of (tetrahydrofuran-3-yl)methanol (51 mg, 0.50 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (97 mg, 0.5 mmol) in degassed 1,4-dioxane (2 mL) sealed in a microwave tube at rt under nitrogen. The solution was heated to 150¡ãC for 30 min in the microwave reactor and cooled to rt. 2) 1-Bromo-4-methoxybenzene (94 mg, 0.50 mmol), potassium carbonate (207 mg, 1.50 mmol) and [1,1?-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with CH2Cl2 (40.8 mg, 0.05 mmol) were added to the solution. The tube was sealed, evacuated and backfilled with nitrogen. Degassed water (1 mL) was added under nitrogen. The resulting mixture was stirred at 120¡ãC for 20 min. The reaction mixture was diluted with EtOAc (25 mL) and water (15 mL), the layers were separated, and the aqueous layer was extracted with EtOAc (15 mL). The combined organic layers were washed with saturated brine (15 mL). The organic layer was dried with MgSO4, filtered and evaporated to afford the crude product. The crude product was purified by preparative HPLC (Waters XSelect CSH C18 ODB column, 5mu silica, 30mm diameter, 100mm length), using decreasingly polar mixtures of water (containing 1percent by volume NH3OH (28-30percent in H2O)) and MeCN as eluents to afford 4-(4-methoxyphenyl)-1-((tetrahydrofuran-3-yl)methyl)-1H-pyrazole (89mg, 69percent) as a beige solid., 5464-12-0

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

Reference£º
Article; Mosallanejad, Arash; Lorthioir, Olivier; Tetrahedron Letters; vol. 59; 18; (2018); p. 1708 – 1710;,
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.5464-12-0,1-(2-Hydroxyethyl)-4-methylpiperazine,as a common compound, the synthetic route is as follows.

5464-12-0, a) 1 -(2-Chloroethyl)-4-methylpiperazine (1-96) Thionyl chloride (2.4 mL; 33 mmol; 1.1 eq) was added to a solution of 2- (4- methylpiperazin-l-yl)ethan-l-ol (4 g; 29 mmol; 1 eq) in dry chloroforme (40 mL). The reaction mixture was stirred at reflux for 4 hours, then, concentrated to dryness. 1M sodium hydroxide solution (100 mL) was added and the aqueous layer was extracted with ethyl acetate (3 x 150 mL). The combined organic layers were washed with saturated sodium chloride (1 x 50 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound, l-(2-chloroethyl)- 4-methylpiperazine in 35percent yield (1.66 g) as an brown oil. 1H NMR (CDC13): 2.36 (s, 3H), 2.59 (m, 8H), 2.79 (t, 2H), 3.64 (t, 2H); MS (ESI+): m/z = 163.1-165.1 [M+H]+.

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

Reference£º
Patent; VIVALIS; GUEDAT, Philippe; BERECIBAR, Amaya; CIAPETTI, Paola; VENKATA PITHANI, Subhash; TROUCHE, Nathalie; WO2013/171281; (2013); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics