Heterocyclic Building Blocks-piperidine

373604-28-5, tert-Butyl 3-fluoro-4-hydroxypiperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1: Sodium hydride (40 mg, 1.0 mmol) was added to a 0C solution of tert-butyl 3-fluoro-4- hydroxypiperidine-1-carboxylate (200 mg, 0.9 12 mmol) in DMF (3.0 mL). The reaction mixture was stirred at 0C for 5 minutes, and then iodomethane (63 jiL, 1.0 mmol) was added. The mixture was slowly warmed to room temperature and stirred for 16 h. The mixture was dilutedwith EtOAc and washed with water and then brine. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by colunm chromatography on silica gel (0 – 70% EtOAc/Hexanes) to afford tert-butyl 3-fluoro-4- methoxypiperidine-1-carboxylate as an oil.

373604-28-5, As the paragraph descriping shows that 373604-28-5 is playing an increasingly important role.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; FISCHER, Christian; BOGEN, Stephane, L.; CHILDERS, Matthew, L.; LLINAS, Francesc Xavier Fradera; ELLIS, J. Michael; ESPOSITE, Sara; HONG, Qingmei; HUANG, Chunhui; KIM, Alexander, J.; LAMPE, John, W.; MACHACEK, Michelle, R.; MCMASTERS, Daniel, R.; OTTE, Ryan, D.; PARKER, Dann, L., Jr.; REUTERSHAN, Michael; SCIAMMETTA, Nunzio; SHAO, Pengcheng, P.; SLOMAN, David, L.; UJJAINWALLA, Feroze; WHITE, Catherine; WU, Zhicai; YU, Yang; ZHAO, Kake; GIBEAU, Craig; BIFTU, Tesfaye; BIJU, Purakkattle; CHEN, Lei; CLOSE, Joshua; FULLER, Peter, H.; HUANG, Xianhai; PARK, Min, K.; SIMOV, Vladimir; WITTER, David, J.; ZHANG, Hongjun; (297 pag.)WO2016/89797; (2016); A1;,
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113310-52-4, 4-(Piperidin-4-yl)aniline is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Substrates NT1-003 (80 mg, 0.32 mmol) and NT1-004 (28.4 mg, 0.32 mmol) were mixed in a microwave tube with EtOH (1 mL). Then 0.1NHC1 (1 mL) was added to the tube. The vessel was sealed and heated to 150 C for 40 minutes. The solvent was removed under reduced pressure, the residue washed with DCM, and filtered to afford 5 -chloro-N2-(4-Q,iperidin-4-yl)phenyl)-1V4-((tetrahydrofuran-2-yl)methyl)pyrimidine-2,4- diamine (NT1-005) as a peach solid (90 mg, 72.0%), mp 160 C (dec.). HPLC 85.6% [R = 7.51 mm, 30% CH3OH in 0.1% TFA water 20 mm]. ?H NMR (400 MHz, Methanol-d4) oe 7.94 (s,1H), 7.49 (d, J= 8.2 Hz, 2H), 7.35 (d, J= 8.4 Hz, 2H), 4.16 (p, J= 6.2 Hz, 1H), 3.86-3.68 (m,2H), 3.65 -3.46 (m, 4H), 3.22-3.09 (m, 2H), 3.00-2.90 (m, 1H), 2.14- 1.82 (m, 8H), 1.69-1.58(m, 1H). ?3C NMR (101 MHz, Methanol-d4) oe 159.20, 151.43, 141.84, 139.72, 135.04, 127.16,122.99, 105.19, 76.74, 67.63, 45.23, 44.15, 39.15, 29.68, 28.54, 25.01. LC-MS (ESI+) m/z388.18965 (M+H) HRMS (ESI+) m/z calculated for C2oH26ClN5O(M+H)388.1899, found,388.1900.

113310-52-4, 113310-52-4 4-(Piperidin-4-yl)aniline 22047841, apiperidines compound, is more and more widely used in various fields.

Reference£º
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; MAHAJAN, Nupam, P.; MAHAJAN, Kiran, N.; LAWRENCE, Nicholas, J.; LAWRENCE, Harshani, R.; WO2015/21149; (2015); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14691-88-4,4-Amino-2,2,6,6-tetramethylpiperidine 1-Oxyl,as a common compound, the synthetic route is as follows.

To a solution of 6-Hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid (2.50 g, 10 mmol), 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl (1.71 g, 10 mmol) and 4-4-Dimethylaminopyridine (DMAP) (0.6 g, 5 mmol) in CH2Cl2 (50 mL) at 0-5¡ã C., EDAC (2.14 g, 11 mmol) in dichloromethane (50 mL) was added dropwise. After the addition was complete, the mixture was stirred at room temperature overnight. The reaction mixture was washed with water (2*50 mL), 1N HCl (20 mL) and saturated Na2CO3 (20 mL) and dried over MgSO4. After MgSO4 was filtered off, the solvent was removed in vacuum to give a solid. The solid was purified by column chromatography (silica gel, EtOAc/Hexane 1:10). The product, 3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-N-(1-nitroxy-2,2,6,6-tetramethylpiperidin-4-yl)-2H-chromene-2-carboxamide, was an orange solid (2.61 g). The yield was 64.7percent. Used as is in the next step.

14691-88-4, 14691-88-4 4-Amino-2,2,6,6-tetramethylpiperidine 1-Oxyl 550942, apiperidines compound, is more and more widely used in various fields.

Reference£º
Patent; Patil, Ghanshyam; Mousa, Shaker A.; US2008/200405; (2008); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.141699-59-4,tert-Butyl 4-((methylsulfonyl)oxy)piperidine-1-carboxylate,as a common compound, the synthetic route is as follows.

To a stirred solution of 4-bromo-pyrazole (10.44 g, 71.03 mmol) in anhydrous DMF (96 mL), cooled to 0¡ã C., was slowly added NaH (60percent in mineral oil) (3.13 g, 78.133 mmol). The solution was stirred for 1 hour at 0¡ã C. 4-Methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl ester (19.82 g, 71.03 mmol) was added slowly and the reaction was heated to 100¡ã C. overnight or until consumption of the pyrazole by NMR. The reaction was cooled to room temperature and water added (20 mL) followed by extraction with EtOAc. The combined extracts were washed with saturated aqueous NaCl (4*20 mL), dried with Na2SO4 and concentrated to afford 4-(4-bromo-pyrazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester as an orange oil. The oil was purified using silica gel chromatography eluding with 10percent EtOAc/hexanes to 25percent EtOAc/hexanes to provide 4-(4-bromo-pyrazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester as a white solid (10.55 g, 45percent yield) with a Rf=0.4 (25percent EtOAc/hexanes, using iodine as the stain). 1H NMR (CDCl3, 400 MHz) delta 7.46 (s, 1H), 7.43 (s, 1H), 4.23 (m, 3H), 2.88 (m, 2H), 2.10 (m, 2H), 1.88 (m, 2H), 1.47 (s, 9H)., 141699-59-4

141699-59-4 tert-Butyl 4-((methylsulfonyl)oxy)piperidine-1-carboxylate 4184869, apiperidines compound, is more and more widely used in various fields.

Reference£º
Patent; AGOURON PHARMACEUTICALS, INC.; US2006/46991; (2006); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.20845-34-5,1-Methyl-2-piperidinemethanol,as a common compound, the synthetic route is as follows.

A mixture of (1-methylpiperidin-2-yl)methanol (74a) (78 mg, 0.61 mmol, 1.3 eq), compound 4d (114 mg, 0.47 mmol), and PPh3 (162.2 mg, 0.61 mmol, 1.3 eq) in dry THF(10 mL) under N2 at 0¡ãC was treated with DIAD (0.12 mL 0.61 mmol) and the reaction mixture was stirred for two days, allowing it to warm to 20 ¡ãC. The solvent was removed under vacuum, and the residue was partitioned between CH2C12 and dil. aq. HC1 (the product did not go into the aqueous layer). The organic layer was separated and washed with aq.KOH, and dried (Na2SO4). Chromatographyon Si02 eluting with 50percent CH2C12/hexanes then50percent CH2C12/EtOAc gave 6-fluoro-2-methyl-4-(( 1 -methylazepan-2-yl)oxy)-9H-xanthen-9- one (74b) (8.0 mg 4.8percent): ?H NIVIR (CDC13) 5 8.34 (dd, J= 8.9, 6.5 Hz, 1H), 7.70 (dd, J= 1.8, 0.8Hz, 1H), 7.25 (dd, J= 9.4, 2.4 Hz, 1H), 7.12-7.07 (m, 2H), 4.62-4.56 (m, 1H), 2.98 (dd, J 13.6, 4.2 Hz, 1H), 2.88 (dd, J 13.6, 7.2 Hz, 1H), 2.75-2.69 (m, 1H), 2.64-2.59 (m, 1H), 2.46 (s, 3H), 2.44 (s, 3H), 2.25-2.17 (m, 1H), 2.02-1.94 (m, 1H), 1.89-1.75 (m, 3H), 1.67-1.58 (m, 1H)., 20845-34-5

As the paragraph descriping shows that 20845-34-5 is playing an increasingly important role.

Reference£º
Patent; AUCKLAND UNISERVICES LIMITED; MARSHALL, Andrew James; BUCHANAN, Christina Maree; REWCASTLE, Gordon William; LU, Guo-Liang; FLANAGAN, Jack Urquhart; BONNET, Muriel; SHEPHERD, Peter Robin; JAMIESON, Stephen Michael Frazer; GAMAGE, Swarnalatha Akuratiya; DENNY, William Alexander; (213 pag.)WO2018/83635; (2018); A2;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.135632-53-0,tert-Butyl (piperidin-4-ylmethyl)carbamate,as a common compound, the synthetic route is as follows.

General procedure: NaBH(OAc)3 (typically 1.4 eq) was added to a solution of amine 5 (typically 1.0 eq) and aldehyde (typically 1.0 eq) in 1,2-dichloroethane (DCE). The mixture was stirred at rt until the conversion was finished as judged by TLC and LC/MS analyses. The reaction mixture was quenched with 10% K2CO3 aqueous solution. The product was extracted with dichloromethane (DCM) (3x). The combined organic layers were washed with brine (1x). Subsequently, the organic layer was dried with anhydrous Na2SO4. The solvent was removed in vacuo to give crude product which was purified by flash column chromatography. Unless mentioned otherwise, cyclohexane/5% TEA: EtOAc/5%TEA and a gradient flow from 100-0% to 50-50% were used.

135632-53-0, The synthetic route of 135632-53-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Adlere; Sun; Zarca; Roumen; Gozelle; Viciano Perpina; Caspar; Arimont; Bebelman; Briddon; Hoffmann; Hill; Smit; Vischer; Wijtmans; de Graaf; de Esch; Leurs; European Journal of Medicinal Chemistry; vol. 162; (2019); p. 631 – 649;,
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476014-76-3, 4-Hydroxy-2-piperidinone is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,476014-76-3

[0242] (6) 4-hydroxypiperidin-2-one (0.80g, 6.94mmol) was dissolved in DMF. DMAP (0.085g, 0.694mmol) and imidazole(0.92g, 13.88mmol) were added. After the resulting mixture was stirred evenly, the solution of TBDPS-Cl (2.3g,8.33mmol) in THF was added and stirred at room temperature overnight. After the reaction completed, the reactionmixture was dried by spinning. Column chromatography afforded colorless oily liquid 0.65g, yield 60percent.[0243] 1H NMR (300 MHz, CDCl3) delta 7.70-7.49 (m, 4H), 7.53-7.30 (m, 6H), 4.24-4.09 (dt, J = 8.9,3.0 Hz, 1H),3.62-3.49(dt, J = 13.0, 6.7 Hz, 1H),3.20-3.08 (dtd, J = 11.7, 5.6, 2.3 Hz, 1H), 2.51-2.35 (d, J = 4.8 Hz, 2H),1.83-1.69(m,2H),1.17-1.00 (s,9H).MS(ESI) m/z :[(M+1)+,158.3]

As the paragraph descriping shows that 476014-76-3 is playing an increasingly important role.

Reference£º
Patent; Shanghai Institute of Materia Medica, Chinese Academy of Sciences; Zhe Jiang Jutai Pharmaceutical Co., Ltd; YANG, Yushe; XUE, Tao; DING, Shi; GUO, Bin; EP2947085; (2015); A1;,
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268550-48-7, tert-Butyl 1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The mixture of tert-butyl l-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate (1.83 g, 7.20 mmol), commercially available 4-bromofuran-2(5H)-one (1.41 g, 8.63 mmol), xantphos (0.416 g, 0.720 mmol), water (0.389 mL, 21.6 mmol) , and potassium carbonate (1.989 g, 14.39 mmol) in toluene (50 mL) was degassed with nitrogen followed by addition of palladium acetate (0.081 g, 0.36 mmol). The resulting mixture was heated at 65 C for 16 h. After filtration through celite, the filtrate was concentrated and the residue was purified on silica gel column using EtOAc /hexane as eluting solvents to give the title compound. LC/MS: (M+l)+: 337.18., 268550-48-7

As the paragraph descriping shows that 268550-48-7 is playing an increasingly important role.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; DING, Fa-Xiang; DONG, Shuzhi; FRIE, Jessica; GU, Xin; JIANG, Jinlong; PASTERNAK, Alexander; TANG, Haifeng; WU, Zhicai; YU, Yang; SUZUKI, Takao; WO2014/15495; (2014); A1;,
Piperidine – Wikipedia
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930785-40-3,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.930785-40-3,tert-Butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate,as a common compound, the synthetic route is as follows.

Example 40; Methyl (3-{2-[9-(4-{[6-amino-2-(2-methoxyethoxy)-8-oxo-7,8-dihydro-9H-purin-9-yl]methyl}benzyl)-1-oxa-4,9-diazaspiro[5.5]undec-4-yl]ethoxy}phenyl)acetate; [Show Image] Step (i); tert-Butyl 4-{2-[3-(2-methoxy-2-oxoethyl)phenoxy]ethyl}-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate; [Show Image] tert-Butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate (769mg, 3mmol) and potassium carbonate (622mg, 4.5mmol) were suspended in dimethylformamide (15ml) and thereto was added at room temperature methyl [3-(2-bromoethoxy)phenyl]acetate (1.09g, 4mmol), followed by stirring at 85C for 15 hours. After being cooled, thereto was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over sodium sulfate. After removal of the solvent by distillation, the residue was purified by silica gel column chromatography to give the object compound 565mg as a colorless oil. Yield 42% 1H NMR (CDCl3) delta7.27-7.23 (1H, m), 6.93-6.78 (3H, m), 4.13-4.06 (2H, m), 3.90-3.65 (4H, br), 3.71 (3H, s), 3.61 (2H, s), 3.22-3.15 (2H, br), 2.73 (2H, br), 2.54 (2H, brs), 2.37 (2H, brs), 2.00-1.91 (2H, br), 1.51-1.41 (2H, br), 1.46 (9H, s).

930785-40-3 tert-Butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate 53302318, apiperidines compound, is more and more widely used in various fields.

Reference£º
Patent; Dainippon Sumitomo Pharma Co., Ltd.; AstraZeneca AB; EP1939202; (2008); A1;,
Piperidine – Wikipedia
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73579-08-5, 1-Methyl-4-(methylamino)piperidine is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

73579-08-5, Example 95 Alternative Synthesis of 2-Chloro-4-{4-cycloheptylamino-6-[methyl-(1-methyl-piperidin-4-yl)-amino}-[1,3,5]triazin-2-ylamino)-phenol (138) To E7 (1.00 g, 2.7 mmol) dissolved in THF (25 mL) was added a solution of N-methyl-4-(methylamino)-piperidine (0.45 mL, 3.1 mmol) in THF (5 mL) followed by addition of 2.5 N NaOH (1.1 mL, 2.7 mmol) and 2.5 mL of water. The reaction mixture was stirred and heated at reflux overnight. The reaction mixture was extracted three times using dichloromethane, the combined organic layers were washed with a brine and dried over sodium sulfate. The sample was concentrated and the resulting solid was dried overnight under vacuum. Column chromatography (silica gel, 100percent methanol) yielded an off-white solid (138) (177 mg, 14percent); mp 68¡ã C.; HPLC: Inertsil ODS 3V C18, 40:30:30 v:v:v [KH2PO4 (0.01 M, pH 3.2):CH3OH:CH3CN], 264 nm, Rt 4.7 min, 99.6percent purity; MS (TOF ES+) m/z 460 (M+H, 55.3), 251 (100), 224 (51.1).

73579-08-5 1-Methyl-4-(methylamino)piperidine 566323, apiperidines compound, is more and more widely used in various fields.

Reference£º
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krlshna Reddy, Velagala Venkata Rama Murali; Sridevi, Bhatlapenumarthy Sesha; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209880; (2004); A1;,
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