Category: piperazines

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.70261-82-4,4-(4-Methylpiperazin-1-ylmethyl)phenylamine,as a common compound, the synthetic route is as follows.

To a degassed solution of N-(4-(2-chloro-4-(2-methoxyethoxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl)-2,5-difluorobenzene sulfonamide (140 mg, 0.224 mmol in l,4-dioxane) was added 4-((4-methylpiperazin-l- yl)methyl)aniline (51 mg, 0.246 mmol), palladium(II) acetate (1 mg, 0.004 mmol), SPhos (3 mg, 0.008 mmol) and cesium carbonate (146 mg, 0.448 mmol). The mixture was heated under microwave irradiation at 150W for 20 min. The organic solvent was removed under vacuum and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated under reduced pressure. The product was purified by silica gel column chromatography using dichloro methane and methanol gradient eluents to give 2,5-difluoro- N-(4-(4-(2-methoxyethoxy)-2-((4-((4-methylpiperazin-l-yl)methyl)phenyl)amino)-7-((2- (trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl)benzenesulfonamide in 41% yield as a pale yellow solid. NMR (500 MHz, CDCh): d 7.63 (d, J = 8.5 Hz, 2H), 7.61 (d, J = 8.3 Hz, 2H), 7.53-7.57 (m, 1H), 7.25 (d, J = 8.3 Hz, 2H), 7.14-7.21 (m, 2H), 7.11 (d, J = 8.5 Hz, 2H), 6.96 (s, 2H), 5.51 (s, 2H), 4.55 (t, J = 4.6 Hz, 2H), 3.69 (t, J = 4.6 Hz, 2H), 3.56 (t, J = 8.3 Hz, 2H), 3.47 (s, 2H), 3.37(s, 3H), 2.48 (br, 8H), 2.29 (s, 3H), 0.92 (t, J = 8.3 Hz, 2H), -0.09 (s, 9H); Mass (ESI) m/z 794.58, 397.79 [M+H+], 70261-82-4

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

Reference£º
Patent; DEVELOPMENT CENTER FOR BIOTECHNOLOGY; DCB-USA LLC; YEN, Shih-Chieh; LIAO, Chu-Bin; WANG, Hui-Chen; CHEN, Po-Ting; PAN, Yu-Chih; LI, Tsung-Hui; CHEN, Bo-Rong; CHIOU, Shian-Yi; (64 pag.)WO2019/133629; (2019); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

57260-71-6, tert-Butyl piperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

57260-71-6, General procedure: To a solution of 3a-3c (3.2mmol) and N, N-diisopropylethylamine (DIEA) (4.8mmol) in DMF (3mL) was added N-Boc-piperazine (3.6mmol), the resulting mixture was heated at 110C for 16h. The reaction mixture was poured into ice water (30mL) and extracted with ethyl acetate (3¡Á30mL), the combined organic layers were washed with brine (2¡Á30mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography with petroleum ether/ethylacetate (1: 3) to obtain 4a-4c.

The synthetic route of 57260-71-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Liu, Yang; Yin, Yanzhen; Zhang, Zhen; Li, Carrie J.; Zhang, Hui; Zhang, Daoguang; Jiang, Changying; Nomie, Krystle; Zhang, Liang; Wang, Michael L.; Zhao, Guisen; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 543 – 551;,
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.639068-43-2,tert-Butyl 3,5-dimethylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

639068-43-2, Step 3 Synthesis of 3,5-Dimethyl-4-(2-trifluoromethyl-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester Triethyl amine (55.6 mg, 0.07 mL, 0.55 mmol) was added to a stirred solution of 2,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester (98.6 mg, 0.45 mmol) followed by 2-trifluoromethyl-benzoyl chloride (95.6 mg, 0.45 mmol) and the resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure to get the residue. The residue thus obtained was purified by column chromatography using 60-120 silica gel and 50percent ethyl acetate in hexane to afford 74 mg (41.71percent yield) of 3,5-dimethyl-4-(2-trifluoromethyl-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester. LCMS Purity: 96.7percent.

As the paragraph descriping shows that 639068-43-2 is playing an increasingly important role.

Reference£º
Patent; Bischoff, Alexander; Subramanya, Hosahalli; Sundaresan, Kumar; Sammeta, Srinivasa Raju; Vaka, Anil Kumar; US2010/160323; (2010); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

393781-71-0, 1-Boc-2-Ethylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 1 ,1-dimethylethyl 2-ethyl-1-piperazinecarboxylate (100mg, 0.467 mmol) in DCM (5ml_) was added di-isopropylethylamine (0.253mL, 1.447 mmol), followed by gradual addition of 4-cyanobenzenesulfonyl chloride (103mg, 0.513 mmol). The reaction mixture was allowed to stir for 1 hour. The reaction mixture was diluted with DCM (1 OmL) and the solution was washed with saturated aqueous sodium bicarbonate solution (1OmL, twice), then with distilled water (1OmL). The organic layer was dried (MgSO4), filtered and reduced in vacuo to yield 1 ,1-dimethylethyl 4-[(4-cyanophenyl)sulfonyl]-2-ethyl-1-piperazinecarboxylate as a crude transparent oil (173mg), MS ES+ve m/z 280 (M+H-100). To 1 ,1-dimethylethyl 4-[(4-cyanophenyl)sulfonyl]-2-ethyl-1-piperazinecarboxylate (173mg, 0.456 mmol) was added hydrogen chloride 1 M solution in 1 ,4 dioxane (1OmL) solution, followed by the addition of 3 drops of water. The reaction mixture was allowed to stir for 14hours. After this time, 5M aqueous HCI (1 ml) was added and the mixture was stirred for 12hours. The reaction mixture was concentrated in vacuo to yield colourless oil. The colourless oil was dissolved in methanol (1 OmL) and passed down a SCX-2 column washing with two column volumes of methanol and eluting the product with 2N ammonia solution in methanol (three column volumes). The fraction containing eluted product was reduced in vacuo to yield 4-[(3-ethyl-1- piperazinyl)sulfonyl]benzonitrile (99mg) as a transparent oil, MS ES+ve m/z 280 (M+H).To a solution of 4-[(3-ethyl-1-piperazinyl)sulfonyl]benzonitrile (99mg, 0.354mol) in tetrahydrofuran (1OmL) was added triethylamine (0.074mL, 0.532mmol) followed by drop wise addition of benzoyl chloride (0.045mL, 0.390mmol). The reaction mixture was allowed to stir for 30minut.es. The reaction mixture was diluted with DCM (1 OmL) and the solution was washed with saturated aqueous sodium bicarbonate solution (1OmL, twice), then 0.1 M hydrochloric acid (1OmL). The organic layer was dried with (MgSO4), filtered and concentrated in vacuo to yield 144mg colourless oil. The oil was dissolved in minimum volume of hot ethyl acetate (~2ml), hot iso-hexane (10ml) was then added and allowed to cool to room temperature. The supernatant was decanted off, and residual solid triturated with diethyl ether (50ml), to yield a white solid (67mg, 37%).1H-NMR (CDCI3) delta 0.65-1.19 (3H, br m), 1.78-1.98 (2H, m), 2.20-2.40 (1 H, m), 2.40- 2.57 (1 H, m), 2.96-3.48 (1 H, m), 3.48-3.96 (3H, m), 4.21-5.01 (1 H, m), 7.28-7.31 (2H, m), 7.36-7.45 (3H, m), 7.81-7.89 (4H, m).MS ES+ve m/z 384 (M+H).The single enantiomers were isolated from the racemic 4-{[3-ethyl-4-(phenylcarbonyl)-1-piperazinyl]sulfonyl}benzonitrile (53mg) via chiral preparative chromatography using the following conditions:- Column: Chiralpak IC (20mm x 250mm, 5mum)- Eluent: Heptane: Ethanol 50:50 v/v pump-mixed – Flow rate =17. Omls/min- U.V. Absorbance (S) 215nm- Autosampler injection (250mul of sample in 20%Heptane/30%EtOH/50%DMF on column)- lsocratic Run time = 30 minutesIsolated enantiomers were analysed via chiral analytical chromatography using the following conditions:- Chiralpak IC (4.6mm x 250mm, 5mum)- Heptane: Ethanol 50:50 v/v pump-mixed – Flow rate =1. Omls/min- U.V. Absorbance (at) 215nm- Autosampler injection (1 Omul of sample in mobile phase on column)- lsocratic Run time = 30 minutesIsolated compounds: Example 5a: Faster running enantiomer (4-{[(3S)-3-ethyl-4-(phenylcarbonyl)-1- piperazinyl]sulfonyl}benzonitrile or 4-{[(3R)-3-ethyl-4-(phenylcarbonyl)-1- piperazinyl]sulfonyl}benzonitrile, 16mg)Retention time 19.37min, 393781-71-0

393781-71-0 1-Boc-2-Ethylpiperazine 18004789, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; GLAXO GROUP LIMITED; BESWICK, Paul, John; CAMPBELL, Alister; CRIDLAND, Andrew; GLEAVE, Robert, James; PAGE, Lee, William; WO2010/102663; (2010); 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.20327-23-5,1-Cyclopropylpiperazine,as a common compound, the synthetic route is as follows.

To 80 mg (0.19 mmol) E-8 in 1 mL dioxane is added 0.12 g (0.93 mmol) 1-cyclopropyl- piperazine and 26 mu. (0.19 mmol) triethylamine and the reaction mixture is stirred for 3 h at 80C. A 1/1 acetonitrile/water mixture is added and the reaction mixture is purified by RP chromatography (C18). Yield: 49 mg (51%). HPLC-MS: M+H = 521; tR = 1.26 min.

20327-23-5, 20327-23-5 1-Cyclopropylpiperazine 4742004, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WUNBERG, Tobias; VEEN, Van Der, Lars; KRAEMER, Oliver; WO2012/101186; (2012); 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.5271-27-2,1-Methyl-3-phenylpiperazine,as a common compound, the synthetic route is as follows.

5271-27-2, 24. (2,4-bis(allyloxy)-5-isopropylphenyl)(4-methyl-2-phenylpiperazin-1-yl)methanone (16) Compound 14 (0.18 g, 0.66 mmol), 1-methyl-3-phenylpiperazine (0.18 g, 0.99 mmol), 1-ethyl-3-(3-dimethylaminopropyl) (0.25 g, 1.33 mmol), 1-hydroxybenzotriazole (0.09 g, 0.66 mmol) and N,N-diisopropylethylamine (0.09 mL, 0.66 mmol) were dissolved in 4 ml of DMF and stirred at 120¡ã C. for 3 hours under a microwave irradiation (Biotage Initiator). The reaction mixture was diluted with ethyl acetate and the organic layer was washed with 1 N HCl solution. It was dried over Na2SO4, concentrated under pressure and purified by MPLC to obtain Compound 16 in a yield of 92percent. Rf=0.24 (3:7 ethyl acetate:hexane).

The synthetic route of 5271-27-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; INDUSTRY ACADEMIC COOPERATION FOUNDATION KEIMYUNG UNIVERSITY; SEO, Young Ho; (32 pag.)US2019/31620; (2019); 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.59878-57-8,1-(Cyclopropylcarbonyl)piperazine,as a common compound, the synthetic route is as follows.

59878-57-8, To a round bottom flask containing Methyl-5-((4-oxo-3-((2-(trimethylsilyl)ethoxy) methyl)- 3,4-dihydrophthalazin-l-yl) methyl)-2-(4,4,5,5-tetramethyl-l,3,2-dioxa borolan-2- yl)benzoate and bis(pinacolato) diboron (2.00 g) was added THF (100 mL) before cooling to 0C. Upon cooling, 2M lithium hydroxide (7 mL, 14 mmol) was added dropwise before allowing to reaction to stir for 30 minutes at 0C. 1M HC1 was then added dropwise to the reaction mixture at 0C until reaching pH 4. The mixture was then extracted with EtOAc (3 x 80 mL) and washed with Brine (3 x 50 mL). The organic phases were combined and the excess solvent removed in vacuo. The crude material (1.4 g) was transferred to a round bottom flask upon which DCM (100 mL), HBTU (2.97 g, 7.84 mmol) and DIPEA (1.36 mL, 7.84 mmol) was added. After stirring at room temperature for 30 minutes, N- cyclopropylcarbonylpiperazine (1.11 mL, 7.85 mmol) was added and the reaction stirred overnight. After stirring for 16 hours, the excess solvent was removed in vacuo and the crude material isolated by flash column chromatography (Pure EtOAc) before purification by reverse phase HPLC was carried out to afford 4-(3-(4-(cyclopropanecarbonyl) piperazine- 1- carbonyl)-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzyl)-2-((2-trimethlsilyl) ethoxy)methyl)phthalazin-l(2/7)-one (419 mg, 0.62 mmol, 22% – three steps) as a white solid in a mixture of rotamers. In each case the shift relating to the minor rotamer has been donated with an asterisk.* *H NMR (400 MHz, CDCb) d = 8.46 (dd, J = 7.8, 1.6 Hz, 1H + 1H*), 7.79 – 7.55 (m, 4H + 4H*), 7.32 – 7.28 (m, 1H + 1H*), 7.14 (bs, 1H + 1H*), 5.59 (s, 2H + 2H*), 4.33 (s, 2H + 2H*), 3.87 – 3.04 (m, 10H + 10H*), 1.28 (s, 12H + 12H*), 1.04 – 0.97 (m, 4H + 4H*), 0.90 – 0.85 (m, 1H + 1H*), 0.83 – 0.71 (m, 2H + 2H*), 0.00 (s, 9H + 9H*); 13C NMR (100 MHz, CDCb) d = 172.3 (1C + 1C*), 171.0 (1C + 1C*), 160.0 (1C + 1C*), 144.7 (1C + 1C*), 142.9 (1C + 1C*), 141.3 (1C + 1C*), 136.3 (1C + 1C*), 133.3 (1C + 1C*), 131.5 (1C + 1C*), 129.2 (1C + 1C*), 128.4 (1C + 1C*), 128.2 (1C + 1C*), 127.7 (1C + 1C*), 125.4 (1C + 1C*), 125.2 (1C + 1C*), 84.1 (2C + 2C*), 79.0 (1C + 1C*), 67.3 (1C + 1C*), 47.3 (1C*), 46.9 (1C), 45.2 (1C*), 44.8 (1C), 41.9 (1C*), 41.7 (2C), 41.4 (1C*), 39.1 (1C + 1C*), 24.9 (4C + 4C*), 18.1 (1C + 1C*), 11.1 (1C + 1C*), 7.66 (2C + 2C*), -1.36 (3C + 3C*) (the carbon bearing the boron substituent is not observed); IR (v, cm 1): 2981, 2889, 2360, 2341, 1641, 1382, 1354, 1146, 1087, 956; HRMS (ESI) for C36H49N4O610B23Na28Si [M+Na]+ requires 694.34429 found 694.34418; Mp: 78 – 80C.

59878-57-8 1-(Cyclopropylcarbonyl)piperazine 2064235, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; OXFORD UNIVERSITY INNOVATION LIMITED; GOUVERNEUR, Veronique; CORNELISSEN, Bart; WILSON, Thomas Charles; (152 pag.)WO2019/186135; (2019); 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

EXAMPLE 7 1-Cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid A mixture of 0.75 g (2.68 mmol) of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid, 1.07 g (10.4 mmol) of 2-methylpiperazine and 30 ml of acetonitrile was refluxed for five hours, then stirred at room temperature overnight. The precipitate was filtered, washed with water/ethanol and acetonitrile, and dried to give 0.42 g of the title compound, mp 189-192 C., 109-07-9

The synthetic route of 109-07-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Warner-Lambert Company; US4920120; (1990); A;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

259808-67-8, 1-Boc-3,3-Dimethylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

9.1: 2,2-Dimethyl-piperazine-1,4-dicarboxylic acid 1-benzyl ester 4-tert-butyl ester To a solution of 18.5 g (82.0 mmol) 3,3-dimethyl-piperazine-1-carboxylic acid tert-butyl ester in 150 mL DCM at RT was added 30.0 mL (174 mmol) DIPEA. The mixture was cooled with ice and a solution of 14.0 mL (93.2 mmol) benzyl chloroformate in 60 mL DCM was added dropwise. The reaction mixture was stirred at RT over night and quenched with saturated aqueous sodium bicarbonate solution. The product was extracted with DCM. The organic layers were combined, dried over sodium sulfate and concentrated in vacuo. Yield: 23.0 g (81%) ESI-MS: m/z=249 (M-BOC+H)+

259808-67-8, The synthetic route of 259808-67-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; HEIMANN, Annekatrin; DAHMANN, Georg; GRUNDL, Marc; MUELLER, Stephan Georg; WELLENZOHN, Bernd; US2013/158042; (2013); 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, 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