Month: March 2022

5166-67-6, Ethyl N-methylpiperidine-3-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: 1-(2-Oxopyrrolidin-1-yl)acetamidoxime (2.40 equiv) was stirred in dry THF with 4A MS for 1 h, and NaH (60% inoil, 3.0 equiv) was added and stirred for 50 mins and then heated at 50 C for 30 min. A solution of an ester 5a~f (1.0 equiv) in THF was added dropwise and the reaction mixture was heated under reflux for 1.5 h. After cooling, solvent was removed from the reaction mixture and the residue was extracted with CH2Cl2. The organic extract was concentrated in vacuo, and the residue was purified by column chromatography on silica gel using chloroform/methanol (30:1~10:1) as eluent to obtain the corresponding compound 6a~f.

5166-67-6, 5166-67-6 Ethyl N-methylpiperidine-3-carboxylate 97981, apiperidines compound, is more and more widely used in various fields.

Reference：
Article; Muthusamy, Selvaraj; Lee, Soo Min; Huang, Minghua; Cho, Nam-Chul; Nam, Ghilsoo; Pae, Ae Nim; Rhim, Hyewhon; Keum, Gyochang; Choi, Kyung Il; Bulletin of the Korean Chemical Society; vol. 37; 7; (2016); p. 1020 – 1028;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.221874-51-7,(R)-tert-Butyl (2-oxopiperidin-3-yl)carbamate,as a common compound, the synthetic route is as follows.

Cuprous iodide (3.6 g, 18 mmol) was added to a mixture of tert-butyl (R)-(2- oxopiperidin-3-yl)carbamate (10 g, 47 mmol), 4-bromo-2-fluoro-l-iodobenzene (14 g, 47 mmol), and potassium phosphate tribasic (15 g, 70 mmol) in dioxane (100 mL), and the mixture was purged with nitrogen for 20 minutes. N^V-dimethylethylenediamine (2.0 mL, 18.7 mmol) was added, and the reaction mixture was stirred at 90 C overnight. The reaction mixture was filtered through celite, washed with ethyl acetate and concentrated in vacuo. The crude product was purified by column chromatography (30% ethyl acetate in pet ether). The mixture was further purified by SFC to give tert- butyl (i?)-(l-(4-bromo- 2-fluorophenyl)-2-oxopiperidin-3-yl)carbamate (3.0 g, 7.8 mmol, 17 % yield) and tert- butyl (i?)-(l-(3-fluoro-4-iodophenyl)-2-oxopiperidin-3-yl)carbamate (1.8 g, 4.1 mmol, 8.8 % yield). Analytical data for Intermediate 2: NMR (300 MHz, CDCh):? ppm 7.30 – 7.37 (m, 2H), 7.10 – 7.18 (m, 1H), 5.46 (s, 1H), 4.27 (m, 1H), 3.53 – 3.68 (m, 2H), 2.54 – 2.66 (m, 1H), 2.01 – 2.12 (m, 2H), 1.46 (s, 9H) ; 19FNMR: -117, MS(ESI) m/z: (0151) 387.2/389.2 (M+H)+. Analytical data for Intermediate 3: NMR (300 MHz, CDCh-d) ? ppm 7.49 – 7.00 (m, 2H), 6.92 – 7.00 (m, 1H), 5.46 (s, 1H), 4.27 (dt, J=11.71, 6.00Hz, 1H), 3.54 – 3.68 (m, 2H), 2.54 -2.66 (m, 1H), 2.01 – 2.12 (m, 2H), 1.74(m, 1H), 1.46 (s, 9H) ; 19F NMR: -117, MS(ESI) m/z: 435.0 (M+H)+.

221874-51-7, As the paragraph descriping shows that 221874-51-7 is playing an increasingly important role.

Reference：
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHIRUDE, Pravin Sudhakar; CHATTOPADHYAY, Amit Kumar; RACHAMREDDY, Chandrasekhar; WURTZ, Nicholas R.; KICK, Ellen K.; (117 pag.)WO2018/227058; (2018); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

140645-24-5, (S)-3-(Aminomethyl)-1-N-Boc-piperidine is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 3 (3.4 g, 20 mmol) in DMF (34 mL), (3S)-3-(aminomethyl)piperidine-1-carboxylic acid tert-butyl ester (5.2 g, 24 mmol) and DIPEA (4.5 mL, 26 mmol) were added. The reaction mixture was stirred at room temperature for 14 h. The reaction mixture was poured into saturated aqueous NH4Cl and extracted with EtOAc. The organic layer was washed with H2O and brine and then dried over Na2SO4 and concentrated in vacuo to give a brown solid. To a solution of the residue in CH2Cl2 (60 mL), TFA (13 mL, 170 mmol) was added and stirred at room temperature for 4 h. The reaction mixture was concentrated in vacuo. The residue was added to saturated aqueous K2CO3 and extracted with (CHCl3-MeOH) (80:20). The organic layer was dried over Na2SO4 and concentrated in vacuo to give 12 (4.2 g, 87%) as a pale solid, 140645-24-5

The synthetic route of 140645-24-5 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Kunikawa, Shigeki; Tanaka, Akira; Mukoyoshi, Koichiro; Nagashima, Shinya; Tominaga, Hiroaki; Chida, Noboru; Tasaki, Mamoru; Shirai, Fumiyuki; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3269 – 3277;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

21319-53-9, 1-Benzylpiperidine-2-carboxylic acid is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 5 1,3,4,11a-Tetrahydro-2H-benzo[b]quinolizin-11(6H)-one. The following is a modification of the procedure reported (Gonzalez Trigo, G.; Alvarez-Builla, J. An. Quim., Ser. C 1980, 76, 12). N-benzylpipecolinic acid (5.10 g, 20.0 mmol) was placed in a 500 mL flask. Polyphosphoric acid (200 g) was added. The mixture was heated in an oil bath gradually to 140 C. with stirring. It was stirred at 140 C. until the bubbling stopped, then cooled to room temperature and poured into ice. The mixture was neutralized with aqueous NaGH (40%) and extracted with ether (5*80 mL). The combined extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo to give a red solid (3.08 g, 77%): m.p. 71-72 C. (benzene); 1H NMR (300 MHz) delta 8.02 (dd, J=7.8, 1.3 Hz, 1 H), 7.50 (td, J=7.3, 1.4 Hz, 1 H), 7.35 (t, J=7.6 Hz, 1 H), 7.23 (d, J=7.6 Hz, 1 H), 3.88 (d, J=15.2 Hz, H-6), 3.68 (d, J=14.9 Hz, H-6), 3.09 (br d, J=11.2 Hz, 1 H), 2.77 (br d, J=10.5 Hz, 1 H), 2.44 (m, 1 H), 2.35 (td, J=11.3, 3.5 Hz, 1 H), 1.90 (br d,J=12.5 Hz, 1 H), 1.32-1.76 (m, 4 H); 13C NMR (75 MHz) delta 195.87, 141.73, 133.53, 130.12, 127.34, 127.00, 126.17, 69.21, 57.14, 56.13, 26.66, 25.02, 23.81.

21319-53-9, 21319-53-9 1-Benzylpiperidine-2-carboxylic acid 2841641, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; American Biogenetic Sciences, Inc.; University College Dublin; US6436954; (2002); B1;,
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.

Example 4 The procedures were carried out in the same manner as in Example 2, except that a toluene (8 g) solution containing 0.60 g (4.3 mmol, 1 mol %) of 2,2,6,6-tetramethylpiperidine was added, dropwise, to phenyl sodium, which had been prepared by reacting 20.0 g (0.870 mol) of sodium dispersion and 48.0 g (0.426 mol) of chlorobenzene in 160 g of toluene, at room temperature, and then the reaction mixture was stirred for 1 hour, to give benzyltrimethylsilane, at the reaction yield of 99.0%.

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

Reference：
Patent; K· I Chemical Industry Co., Ltd.; US6024897; (2000); A;,
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 500 ml four-necked round bottom flask equipped with a mechanical stirrer, a reflux, a thermometer, a funnel and a septum are added 40 g of water, 10 g K2CO3 (99%; 7,24·10-2 mol), 5 g 2,2,6,6-tetramethylpiperidine (99%; 3,53·10-2 mol) and 50 g toluene. Then, a solution of 21,702 g of Oxone (Monopersulfate, DuPont Specialty Chemicals, USA) (3,53·10-2 mol) in 100 g water is slowly added to the 500 ml 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 for 30 minutes, and the organic phase becomes progressively red due to the formation of 2,2,6,6-tetramethylpiperidine-1-oxide (TEMPO). Then, the reaction medium is heated at 40 C. for further 30 minutes. The reaction medium is then cooled at room temperature, 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. 11,124 g FeSO4.7H2O (4·10-2 mol) are then slowly added under an argon atmosphere and while stirring vigorously. Then, a degassed mixture of 100 ml methanol and 36,7 g of styrene (3,53 10-1 mol) are added rapidly to the reaction flask and the temperature is increased to 40 C. Finally, a solution of 13,71 g hydrogen peroxide (35%; 0.1412 mol) in 15 g methanol is added slowly (dropwise) for 28 minutes while keeping the temperature between 30 and 40 C. (with an exothermic reaction). When the addition is complete, the reaction mixture is allowed to react while stirring vigorously by room temperature for 2 h 30 mins. [0108] The brown solution is then filtered and the residual styrene, hydrogen peroxide and methanol are then removed in vacuo at 50 C. To the viscous brown residue obtained is added 100 g of CH2Cl2 and 30 g of water, and then HCl is added until the pH is 3. The organic phase is then washed 2 times with an acidic solution (pH is 3) in order to remove the excess 2,2,6,6-tetramethylpiperidine. The organic phase is finally dried under MgSO4, filtered and dried in vacuo at 50 C. 2,79 g of a viscous light yellow oil is obtained.Synthesis of 1-phenyl-1-(2′,2′,6′,6′-tetramethyl-1′-piperidinyloxy)-2-hydroxyethane 1 using Oxone (potassium monopersulfate, DuPont Specialty Chemicals, USA) as the oxidizing agent: scale-up To a 6 l four-necked round bottom flask equipped with a mechanical stirrer, a reflux condenser a thermometer, a funnel and a septum are added 634 g of water, 158,42 g K2CO3 (99%; 1,146 mol), 79,21 g 2,2,6,6-tetramethylpiperidine (99%; 5,607·10-1 mol) and 792,1 g toluene. Then, a solution of 343,8 g of Oxone (Monopersulfate, DuPont Specialty Chemicals, USA) (5,59·10-1 mol) in 1584 g water is slowly added (over a period of 1 h 40 mins.) to the 6 l flask while stirring vigorously (slightly exothermic reaction) and the flask is placed in a water bath at room temperature. After the addition is complete, the reaction medium is stirred at room temperature for 30 minutes, and the organic phase becomes progressively red due to the formation of 2,2,6,6-tetramethylpiperidine-1-oxide (TEMPO). Then, the reaction medium is heated at 40 C. for a further 30 minutes. [0126] The reaction medium is then cooled at room temperature, 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. 176,23 g FeSO4·7H2O (6,34·10-1 mol) are then slowly added in an argon atmosphere, while stirring vigorously. Then, a degassed mixture of 1584,2 g of methanol and 581,4 g of styrene (5,582 mol) is added rapidly to the reaction flask and the temperature is increased to 30 C. Finally, a solution of 217,19 g hydrogen peroxide (Merck, 35%; 2,235 mol) in 237,63 g methanol is slowly added (dropwise) for 5 h 40 minutes while keeping the temperature at between 30 and 40 C. When the addition is complete, the reaction mixture is allowed to react while stirring vigorously at room temperature for 15 h. [0127] The brown solution is then filtered and the residual styrene, hydrogen peroxide and methanol are then removed in vacuo at 50 C. To the viscous brown residue obtained is added 1500 g of CH2Cl2 and 475 g of water, and then HCl is added until the pH is 3. The organic phase is then washed twice with an acidic solution (pH=3) in order to remove the excess 2,2,6,6-tetramethylpiperidine. The organic phase is finally dried under MgSO4, filtered and dried in vacuo at 50 C. 121 g of a viscous light yellow oil is obtained. [0128] In order to remove polystyrene formed during the reaction (optional step), the product is dissolved in chloroform and then precipitated in methanol. After filtration, the methanol phase is dried in vacuo and this operation is repeated once to obtain 71,35 g of a slightly yellow oil. This oil contains 1 and very low molecular weight polystyrene. The alkoxyamine 1 may be purified by flash chromatography or by high vacuum dist…

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

Reference：
Patent; Detrembleur, Christophe; Gross, Thomas; Meyer, Rolf-Volker; US2003/236368; (2003); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

914988-10-6, tert-Butyl 3-cyano-4-oxopiperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

914988-10-6, A mixture of tert-butyl 3 -cyano-4-oxopiperidine- 1 -carboxylate (310 g, 1.38 mol) and hydrazine mono-hydrate (140 mL, 2.08 mol) in EtOH (1.5 L) was heated to 60 C for 2 h. The mixture was concentrated in vacuo to give the crude product that was dissolved in EtOAc (1 L) and washed with water (1 L x 2). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford the title compound (230 g, 70%) as a colorless solid. ?HNMR (400 IVIHz, CD3OD) 4.28 (s, 2H), 3.66- 3.63 (m, 2H), 2.62-2.59 (m, 2H), 1.49 (s, 9H).

The synthetic route of 914988-10-6 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; CYR, Patrick; BRONNER, Sarah; ROMERO, F. Anthony; MAGNUSON, Steven; TSUI, Vickie Hsiao-Wei; MURRAY, Jeremy M.; WAI, John; LAI, Kwong Wah; WANG, Fei; CHEN, Kevin X.; (351 pag.)WO2017/205538; (2017); 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.683233-14-9,(R)-tert-Butyl 2-(aminomethyl)piperidine-1-carboxylate,as a common compound, the synthetic route is as follows.

Into a lOO-mL 3 -necked round-bottom flask, was placed a solution of tert-butyl (2R)- 2-(aminomethyl)piperidine-l-carboxylate (500 mg, 2.33 mmol, 1.00 eq.) in dichloromethane (20 mL). This was followed by the addition of TEA (472 mg, 4.66 mmol, 2.00 eq.) dropwise with stirring at -60 C. To this was added 4-nitrophenyl chloroformate (940 mg, 4.66 mmol, 2.00 eq.) in several batches at -60 C. The resulting solution was stirred for 2 h at rt. The reaction was then quenched by the addition of water (20 mL). The resulting solution was extracted with dichloromethane (2 x 20 mL) and the organic layers combined. The resulting mixture was washed with sodium chloride. (1 x 20 mL) The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate:petroleum ether (10:90). This resulted in 600 mg (68%) oftert-butyl(2R)-2-[[(4- nitrophenoxycarbonyl)amino]methyl]piperidine-l-carboxylate as yellow oil., 683233-14-9

As the paragraph descriping shows that 683233-14-9 is playing an increasingly important role.

Reference：
Patent; PRINCIPIA BIOPHARMA INC.; LOU, Yan; OWENS, Timothy Duncan; BRAMELD, Kenneth Albert; GOLDSTEIN, David Michael; (302 pag.)WO2019/99582; (2019); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

109384-19-2, tert-Butyl 4-hydroxypiperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Preparation Example 1 (4-(4-(trifluoromethoxy)phenoxy)piperidine (I-6a) P-trifluoromethoxy phenol (32.7 g, 184 mmol), N-Boc-4-hydroxy piperidine (37 g, 184 mmol) and triphenylphosphine (48.3 g, 184 mmol) were dissolved in dry THF (500 mL), DIAD (37.2 g, 184 mmol) was added dropwise while cooling in ice-bath, followed by stirring overnight at room termperature. THF were spun out, residuals were extracted by petroleum ether, extracting solution was concentrated to give 71.2 g light yellow oily matter, crude product yield was more than 100%, directly put into the next reaction step. The crude products obtained from the previous step (66.5 g, 184 mmol) were dissolved in TFA (500 mL), stirring at room temperature. After 3 h, TFA were spun out, add water to residuals, use NaOH solution to adjust pH to above pH 10, extract by ethyl acetate, extracting solution was concentrated followed by column chromatography to give 35.3 g white solid, yield was 73%. ESI-LR: 262.1 [M+1]+.

109384-19-2, 109384-19-2 tert-Butyl 4-hydroxypiperidine-1-carboxylate 643502, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Wang, Tiancai; Xin, Ting; Fan, Houxing; Chen, Yilang; US2013/143864; (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.10338-57-5,4-(Piperidin-1-yl)benzaldehyde,as a common compound, the synthetic route is as follows.

General procedure: Chalcones analogs were synthesized by Claisen-Schmidt condensation reaction using appropriate equimolar amounts of substituted acetophenones and benzaldehydes in MeOH. NaOH was dissolved in the least amount of water and added dropwise (3mmol) (Scheme 1). Reactions were stirred overnight. All reactions were monitored by TLC using appropriate solvent or mixture of solvents. When the reaction was complete, the obtained precipitate was filtered, washed with cold methanol and dried under vacuum. The crude products were crystallized from different solvent systems based on their solubility or purified by column chromatography to give pure crystalline compounds.

10338-57-5, As the paragraph descriping shows that 10338-57-5 is playing an increasingly important role.

Reference：
Article; Elkhalifa, Dana; Siddique, Abu Bakar; Qusa, Mohammed; Cyprian, Farhan S.; El Sayed, Khalid; Alali, Feras; Al Moustafa, Ala-Eddin; Khalil, Ashraf; European Journal of Medicinal Chemistry; vol. 187; (2020);,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem