Category: 768-66-1

768-66-1, 2,2,6,6-Tetramethylpiperidine is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,768-66-1

A dry and argon-flushed 500 mL Schlenk flask, equipped with a magnetic stirring bar and a rubber septum, was charged with i-PrMgCl·LiCl(1.31 M in THF, 229 mL, 300 mmol). Then, TMPH (52.0 mL, 306 mmol,1.02 equiv) was added and the mixture was stirred until gas evolution ceased (48 h). The freshly prepared TMPMgCl·LiCl (5) solution was titrated prior to use at 0 C with benzoic acid and by using 4-(phenylazo)diphenylamine as indicator.

768-66-1 2,2,6,6-Tetramethylpiperidine 13035, apiperidines compound, is more and more widely used in various fields.

Reference：
Article; Ziegler, Dorothee S.; Klier, Lydia; Mueller, Nicolas; Karaghiosoff, Konstantin; Knochel, Paul; Synthesis; vol. 50; 22; (2018); p. 4383 – 4394;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

768-66-1, 2,2,6,6-Tetramethylpiperidine is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,768-66-1

n-BuLi (2.5M in hexanes, 2.27 mL, 5.67mmol) was added to cold(-50 C) anhydrous THF (20 mL) under nitrogen. 2,2, 6, 6-Tetramethylpiperidine (0.957, 0.8 g, 5.67mmol) was then added and the mixture stirred at-78 C for 30 min. A solution of the title compound of Preparation 53 (0.5 g, 2.68mmol) in THF (5 mL) was added dropwise and the mixture was stirred at-78 C for 60 min. Then, iodine (1.51 g, 5.94mmol) was added and the mixture was stirred at that temperature for 90 min and then warmed to r. t. The mixture was quenched with methanol and the residual iodine destroyed with sat. sodiumthiosulphate (aq. ). The mixture was concentrated in vacuo, partitioned between ethyl acetate and water and the organic layer was washed with water, dried and evaporated to give an oil which was purified by column cromatography (n-Hex/EtOAc 4: 1) to afford the title compound (87% yield) as an oil which crystallised. 8 (CDCI3) : 4.22 (s, 3H), 7.47 (m, 3H), 7.96 (m, 2H), 8.29 (s,1 H).

768-66-1 2,2,6,6-Tetramethylpiperidine 13035, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; ALMIRALL PRODESFARMA, S.A.; WO2005/49581; (2005); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

768-66-1, 2,2,6,6-Tetramethylpiperidine is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,768-66-1

General procedure: Compound 4 0.2 g (0.41 mmol) and 25 muL piperdine (0.82 mmol) was added to the 1.0 mL dried CH2Cl2.Anhydrous Na2CO3 20 mg was then added to the mixture, which was stirred for 12 h. The mixturewas washed with the distilled water, the organic phase was separated and dried over anhydrousNa2SO4, and then concentrated viarotary evaporation. The crude product was purified by silica gelchromatography with petroleum ether-acetone-strong ammonia water (v/v/v, 8/1/0.1) as the eluentto gain 0.18 g yellow solid compound 5a in 90% yield.

768-66-1 2,2,6,6-Tetramethylpiperidine 13035, apiperidines compound, is more and more widely used in various fields.

Reference：
Article; Feng, Xiu E.; Wang, Qin Jin; Gao, Jie; Ban, Shu Rong; Li, Qing Shan; Molecules; vol. 22; 12; (2017);,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

768-66-1, 2,2,6,6-Tetramethylpiperidine is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

768-66-1, 0.71 g (5.0 mmol) 2,2,6,6-tetramethylpiperidine and 0.95 g (5.0 mmol) p-toluenesulfonic acid monohydrate were mixed in 15 mL acetone, the mixture was stirred for 30 mins at room temperature (15-20C), evaporation of the solvent gave the crude product, which was washed with 30 mL n-hexane to give a pure 2,2,6,6-tetramethylpiperidinium tosylate (1.63 g) as a white crystal, the yield is 98%. m.p.: 219.4-220.1C (reference4m.p. = 218-219C); 1H NMR (400 MHz, CDCl3) delta 8.00 (br, 2H), 7.77 (d, J = 8.0 Hz, 2H), 7.19 (d, J= 8.0 Hz, 2H), 2.37 (s, 3H), 1.69-1.58 (m, 6H), 1.49 (s, 12H) ppm; 13C NMR (100 MHz, CDCl3) delta 142.69, 139.95, 128.78, 125.89, 56.78, 34.52, 27.22, 21.34, 16.32 ppm; IR (KBr): 3425, 2997, 2924, 2872, 2838, 2505, 1614, 1485, 1389, 1275, 1227, 1161, 1120, 1034, 1009, 833 cm-1.

768-66-1 2,2,6,6-Tetramethylpiperidine 13035, apiperidines compound, is more and more widely used in various fields.

Reference：
Article; Gao, Lan; Liu, Taoping; Tao, Xiaochun; Huang, Yongmin; Tetrahedron Letters; vol. 57; 44; (2016); p. 4905 – 4909;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

768-66-1,768-66-1, 2,2,6,6-Tetramethylpiperidine is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

In a 1L four-necked round bottom flask equipped with a mechanical stirrer, a reflux, a thermometer, a funnel and a septum are added 80 g of water, 20 g K2CO3 (99%; 1.44·10-1 mol), 20 g 2,2,6,6-tetramethylpiperidine (99%; 1.41·10-1 mol) and 150 g toluene. Then, a solution of 31.3 g of peracetic acid (35 wt %, Aldrich; 1.44·10-1 mol) in 300 g water is slowly added to the 1L flask while stirring vigorously (with a slightly exothermic reaction) and the flask is placed in a water bath at room temperature. After the addition, the reaction medium is stirred at room temperature overnight, and the organic phase becomes progressively red due to the formation of 2,2,6,6-tetramethylpiperidine-1-oxide (TEMPO). [0108] Then, the stirring is terminated and the water phase is removed from the reaction flask. The red organic phase is then degassed by bubbling argon for 10 minutes. 11.82 g azobisisobutyronitrile (AIBN, 7.2·10-2 mol) are then slowly added by small portions under an argon atmosphere and while stirring vigorously. Then, 100 g of degassed toluene is added rapidly to the reaction flask and the temperature is increased to 60 C. After 24 h at 60 C., the solution is cooled at room temperature. Finally, this organic solution is washed 3 times with water (pH=3) and then, dried with Na2SO4. After drying under vacuum at 50 C., 17.95 g of crude alkoxyamine 1 is collected.

The synthetic route of 768-66-1 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Detrembleur, Christophe; Grob, Thomas; Meyer, Rolf-Volker; US2004/2606; (2004); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.768-66-1,2,2,6,6-Tetramethylpiperidine,as a common compound, the synthetic route is as follows.,768-66-1

2,3-Dichloro-4-iodo-pyridine (I-1) To a solution of n-BuLi (27.6 mL, 69 mmol, 2.5 M in hexanes) in dry Et2O (150 mL) cooled at -78 C., under a nitrogen atmosphere, was added 2,2,6,6-tetramethylpiperidine (11.64 mL, 69 mmol) dropwise. The resulting r.m. was stirred at -78 C. for 10 min, and then a solution of 2,3-dichloropyridine (10 g, 67.57 mmol) in dry THF (75 mL) was added dropwise. The mixture was stirred at -78 C. for 30 min and then a solution of iodine (25.38 g, 100 mmol) in dry THF (75 mL) was added. The mixture was allowed to warm to r.t. overnight, quenched with Na2S2O3 (aq sat. sol.) and extracted twice with EtOAc. The combined organic extracts were washed with NaHCO3 (aq. sat. sol.), dried (Na2SO4) and concentrated in vacuo. The crude residue was precipitated with heptane, filtered off and dried to yield intermediate I-1 (8.21 g, 44%) as a pale cream solid.

768-66-1 2,2,6,6-Tetramethylpiperidine 13035, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Janssen Pharmaceuticals, Inc.; Andres-Gil, Jose Ignacio; Alcazar-Vaca, Manuel Jesus; Cid-Nunez, Jose Maria; Trabanco-Suarez, Andres Avelino; Bormans, Guy Maurits R.; Celen, Sofie Jeanne Leopoldine; Koole, Michel; US2013/230459; (2013); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.768-66-1,2,2,6,6-Tetramethylpiperidine,as a common compound, the synthetic route is as follows.,768-66-1

2,2,6,6-Tetramethylpiperidine (18.7 mL, 1 10.5 mmol) is added overtetrahydrofuran (200 mL), and solution is cooled under nitrogen at -78C. 2.5 M solution of butyl lithium in hexane (37.2 mL, 93 mmol) is added and mixture is stirred for 30 min at -78C. Over the fresh lithium 2,2,6,6-tetramethylpiperidine solution is added a solution of tert-butyl spiro[4,5-dihydrothieno[2,3-c]pyran-7,4′-piperidine]-l’- carboxylate (20 g, 58.2 mmol) in tetrahydrofuran (90 mL) keeping temperature below -70C. After 20 min a solution of N-fluorobenzenesulfonimide (30.26 g, 93.07 mmol) in tetrahydrofuran (200 mL) previously cooled under nitrogen at -20C is added via cannula. After 1 hr. stirring, water (20 mL) and aqueous solution of ammonium chloride (50 mL) are added. Then, organic layer is separated and the aqueous is washed twice with methyl t-butyl ether (2 x 25 mL). Organics are combined and solvent is evaporated under reduced pressure. Crude material is purified by normal phase HPLC using hexane/ methyl t-butyl ether as solvents to give tert-butyl 2- fluorospiro[4,5-dihydrothieno[2,3-c]pyran-7,4′-piperidine]-r-carboxylate in 50% yield. MS (m/z): 328 (M+l).

The synthetic route of 768-66-1 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ELI LILLY AND COMPANY; BENITO COLLADO, Ana Belen; DIAZ BUEZO, Nuria; JIMENEZ-AGUADO, Alma Maria; LAFUENTE BLANCO, Celia; MARTINEZ-GRAU, Maria Angeles; PEDREGAL-TERCERO, Concepcion; TOLEDO ESCRIBANO, Miguel Angel; WO2011/60217; (2011); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

768-66-1, 2,2,6,6-Tetramethylpiperidine is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

768-66-1, Example 12 (+)-Dimenthyl (1S, 2S)-Cyclopropane-1,2-dicarboxylate. A 2.5 M solution of butyllithium in hexane (56.9 ml, 142.2 mmol) was added to 180 ml of dry tetrahydrofuran (THF), cooled to -20C. 2,2,6,6-Tetramethylpiperidine (24 ml, 142.2 mmol) was added dropwise over a period of 10 minutes.. The resulting solution of lithium 2,2,6,6-tetramethylpiperidide (LTMP) was cooled to -78C and stirred for 30 minutes.. A solution of (-)-dimenthyl succinate (26.75 g, 67.7 mmol) in THF (60 ml) was then added over a period of 1 h.. The resulting yellow solution was stirred for 1 h.. Thereafter, bromochloromethane (4.39 ml, 67.7 mmol) was added and the reaction mixture stirred for 2 h.. The reaction was quenched by adding isobutyraldehyde (22.46 ml, 27.08 mmol).. After stirring for further 30 minutes, the mixture was poured into ice-cooled 1N hydrochloric acid (250 ml) and the aqueous layer was extracted with diethyl ether (3×150 ml).. The combined organic layers were washed with saturated sodium chloride (250 ml), dried over sodium sulphate and concentrated with a rotary evaporator.. The residue was chromatographed on silica gel (petroleum ether/diethyl ether = 98/2).. An additional flash chromatography on silica gel (petroleum ether/diethyl ether = 98/2) afforded the pure title compound. Yield 33% mp: 95-96C [alpha]D25 = -18.8 (c = 1, CHCl3) 1H-NMR (CDCl3) delta: 0.70-2.20-(complex, 20 H); 0.75 (d, 6H, J = 7 Hz); 0.9 (d, 9H, J = 6.8 Hz); 2.15 (dd, 2H, J = 7.6, 8.7 Hz); 4.7 (dt, 2H, J = 4.3, 10.7 Hz). 13C-NMR (CDCl3) delta: 15.2; 16.4; 20.6; 21.9; 22.2; 23.6; 26.3; 31.3; 34.2; 40.8; 47.0; 74.9; 171.2.

768-66-1 2,2,6,6-Tetramethylpiperidine 13035, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Newron Pharmaceuticals S.p.A.; EP1424333; (2004); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.768-66-1,2,2,6,6-Tetramethylpiperidine,as a common compound, the synthetic route is as follows.

A solution of 2,2,6,6-tetramethylpiperidine (0.567 ml, 3.36 mmol) in dry tetrahydrofurane was cooled in a Schlenk tube to -20 C. N-Butyllithium in hexane (1.6 M, 2.0 ml) was added. The resulting orange solution was stirred for 10 min at -20 C. and was then cooled to -78 C. A solution of N-Butyloxycarbonylindole (0.652 g, 3 mmol) in a small amount of dry tetrahydrofurane was added. Stirring was continued for 90 min at -78 C. before a fresly prepared 1.5 M Zinc chloride solution i tetrahydrofurane (3.3 ml) was added. The reaction mixture was allowed to reach room temperature slowly. This yellow mixture was added to a flask containing bis(tri-t-butylphosphine) palladium (50 mg) and 4-bromo-nitobenzene ((0,509 g, 2.25 mmol). After stirring for 1 h at room temperature the temperature was raised to 60 C. over night. The reaction mixture was diluted with dichloromethane (20 ml) and was washed with saturated aqueous ammonium chloride (2×30 ml). The organic layer was dried (magnesium sulfate) and concentrated under reduced pressure. The residue was filtered hot in heptane and then crystalized to give the title compound in 63% yield (0.480 g). 1H NMR (400 MHz, CHLOROFORM-D), delta ppm 1.33 (m, 9 H), 6.61 (s, 1 H), 7.27 (m, 1 H), 7.36 (t, J=7.83 Hz, 1 H), 7.56 (m, 3 H), 7.67 (d, J=8.08 Hz, 2 H), 8.21 (d, J=8.59 Hz, 1 H).

768-66-1, 768-66-1 2,2,6,6-Tetramethylpiperidine 13035, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Novo Nordisk A/S; US2007/10559; (2007); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

768-66-1, 2,2,6,6-Tetramethylpiperidine is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

768-66-1, 2,2,6,6-Tetramethylpiperidine (2.78 g) was dissolved in anhydrous chloroform (80 ml), and triethylamine (10.1 g) was added thereto. Subsequently, chloroglyoxylic acid ethyl ester (5.40 g) dissolved in anhydrous chloroform (5 ml) was added at 0C, and the mixture was stirred at room temperature for 20 hr. A saturated aqueous sodium hydrogencarbonate solution was added thereto, and the organic layer was separated. The organic layer was washed with saturated brine and was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel, eluting with n-hexane : ethyl acetate (4 : 1) mixed solvent to give N-(glyoxylic ethyl ester)-2,2,6,6-tetramethylpiperidine (4.50 g, yield 94%). 1H-NMR (CDCl3, 400 MHz): 0.85 (t, J = 6.8 Hz, 3H), 1.46 (s, 12H), 1.67 (s, 3H), 4.25 (q, J = 6.8 Hz, 2H) N-(Glyoxylic ethyl ester)-2,2,6,6-tetramethylpiperidine (4.50 g) was dissolved in tetrahydrofuran (100 ml), lithium aluminium hydride (2.14 g) was added thereto at 0C, and the mixture was then heated under reflux for one hr. The excess reagent was decomposed with sodium sulfate decahydrate, followed by filtration through Celite. The filtrate was concentrated under the reduced pressure to give the title compound (3.40 g, yield 100%). 1H-NMR (CDCl3, 400 MHz): 1.02 (s, 12H), 1.41 – 1.65 (m, 6H), 2.68 – 2.72 (m, 2H), 2.95 (br s, 1 H), 3.41 – 3.45 (m, 2H)

As the paragraph descriping shows that 768-66-1 is playing an increasingly important role.

Reference：
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1566379; (2005); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem