Day: March 17, 2022

14813-01-5, 1-Benzylpiperidin-3-ol is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: The alcohol (1.0 equiv.) was dissolved in CH2Cl2 at room temperature.The solution was stirred, and isocyanate (1.2 equiv.) wasadded, followed by 4-DMAP (0.1 equiv.). After 24 h, the solvent wasevaporated and the crude product was purified by flash columnchromatography., 14813-01-5

14813-01-5 1-Benzylpiperidin-3-ol 85773, apiperidines compound, is more and more widely used in various fields.

Reference：
Article; ?akelj, Simon; Brazzolotto, Xavier; Gobec, Stanislav; Juki?, Marko; Knez, Damijan; Ko?ak, Urban; Kos, Janko; Nachon, Florian; Pi?lar, Anja; Stra?ek, Nika; Zahirovi?, Abida; European Journal of Medicinal Chemistry; vol. 197; (2020);,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

888952-55-4,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.888952-55-4,Methyl 1-Boc-3-methylpiperidine-3-carboxylate,as a common compound, the synthetic route is as follows.

A solution of HCl in MeOH (20 mL, 4M) was added 1-tert-butyl 3-methyl 3-methylpiperidine-1, 3-dicarboxylate (2 g, 7.7 mmol) , and the mixture was stirred at room temperature for 16 hours. The mixture was concentrated to give methyl 3-methylpiperidine-3-carboxylate which is used to next step without further purification.

As the paragraph descriping shows that 888952-55-4 is playing an increasingly important role.

Reference：
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph A.; ALHASSAN, Abdul-Basit; BOGA, Sobhana Babu; GAO, Xiaolei; GUIADEEN, Deodialsingh; WANG, Jyhshing; YU, Wensheng; CAI, Jiaqiang; LIU, Shilan; WANG, Dahai; WU, Hao; YANG, Chundao; (260 pag.)WO2016/106623; (2016); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

19365-08-3, 3-Hydroxypiperidin-2-one is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Potassium carbonate or caesium carbonate (1.5-2.5 eq.) was baked in a reaction vessel under reduced pressure. It was cooled to RT and flooded with argon. Palladium acetate (0.1-0.36 eq.), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (Xantphos, 0.18-0.36 eq.) and dioxane (0.04-0.12M) were added, and the suspension was degassed in an argon stream at room temperature for 10 min. Subsequently, the appropriate amide (1.0-1.2 eq.) and the appropriate 7-chloro-4-oxo-1,4-dihydro-1,8-naphthyridine (1.0 eq.) were added. The mixture was stirred at 80-110 C. for 1 h (or until conversion was complete by analytical HPLC or thin-layer chromatography with appropriate eluent mixtures). The mixture was cooled to RT and all volatile components were removed under reduced pressure, or alternatively the reaction mixture was poured into water, the pH was adjusted to pH 1 with 1M aqueous hydrochloric acid, the mixture was extracted with ethyl acetate, the combined organic phases were washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate and filtered, and the solvent was removed under reduced pressure. The crude product was then purified either by normal phase chromatography (eluent: cyclohexane/ethyl acetate mixtures or dichloromethane/methanol mixtures) or preparative RP-HPLC (water/acetonitrile gradient). According to GP2, 150 mg (273 mumol, 96% purity) of the compound from Example 73A were reacted with 31.4 mg (273 mumol) of 3-hydroxy-2-piperidone in the presence of 56.5 mg (409 mumol) of potassium carbonate, 6.1 mg (27 mumol) of palladium(II) acetate and 32 mg (55 mumol) of Xantphos in 2.7 ml of dioxane. The residue was purified by flash chromatography (cyclohexane/ethyl acetate gradient) and preparative HPLC (column: Chromatorex C18, 10 mum, 125*30 mm, solvent: acetonitrile/0.05% formic acid gradient (0 to 3 min 10% acetonitrile, to 35 min 90% acetonitrile and for a further 3 min 90% acetonitrile). 69.8 mg (42% of theory, 100% purity) of the title compound were obtained. 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=11.29 (d, 1H), 8.88 (s, 1H), 8.70 (d, 1H), 8.19-8.10 (m, 1H), 7.93-7.77 (m, 1H), 7.67-7.48 (m, 5H), 7.40-7.31 (m, 1H), 6.53-6.42 (m, 1H), 5.53-5.46 (m, 1H), 4.27-4.18 (m, 1H), 3.71-3.59 (m, 1H), 3.54-3.41 (m, 1H), 2.12-2.02 (m, 1H), 1.84-1.73 (m, 2H), 1.71-1.58 (m, 1H). LC-MS (Method 3): Rt=2.18 min; 607 [M+H]+. 58 mg of the title compound (racemic diastereomer mixture) were separated into the enantiomeric diastereomers by chiral HPLC (preparative HPLC: column: Chiralcel OZ-H 5 mum 250×20 mm; eluent: 75% ethanol, 25% isohexane; temperature: 40 C.; flow rate: 15 ml/min; UV detection: 220 nm). This gave (in the sequence of elution from the column) 14 mg of diastereomer 1 (enantiomer A) (99% de) Rt=6.63 min, 12 mg (99% de) of diastereomer 2 (enantiomer A) Rt=7.71 min, 11 mg (99% de) of diastereomer 1 (enantiomer B) Rt=12.9 min, and 18 mg (99% de) of diastereomer 2 (enantiomer B) Rt=18.3 min. [Analytical HPLC: column: Chiralcel OZ-H 5 mum 250×4.6 mm; eluent: 75% ethanol, 25% isohexane; temperature: 40 C.; flow rate: 1 ml/min; UV detection: 220 nm] Diastereomer 1 (enantiomer A) was additionally purified by means of preparative HPLC (column: Chromatorex C18, 10 mum, 125×30 mm, solvent: acetonitrile/0.05% formic acid gradient; (0 to 3 min. 10% acetonitrile to 35 min. 90% acetonitrile and a further 3 min. 90% acetonitrile)), and 10.4 mg (6.2% of theory, 99% purity) of the title compound from Example 207 were obtained. Diastereomer 2 (enantiomer A) was additionally purified by means of preparative HPLC (column: Chromatorex C18, 10 mum, 125×30 mm, solvent: acetonitrile/0.05% formic acid gradient; (0 to 3 min. 10% acetonitrile to 35 min. 90% acetonitrile and a further 3 min. 90% acetonitrile)), and 8.4 mg (5% of theory, 99% purity) of the title compound from Example 208 were obtained. Diastereomer 1 (enantiomer B) was additionally purified by means of preparative HPLC (column: Chromatorex C18, 10 mum, 125×30 mm, solvent: acetonitrile/0.05% formic acid gradient; (0 to 3 min. 10% acetonitrile to 35 min. 90% acetonitrile and a further 3 min. 90% acetonitrile)), and 8.7 mg (5% of theory, 99% purity) of the title compound from Example 209 were obtained. Diastereomer 2 (enantiomer B) was additionally purified by means of preparative HPLC (column: Chromatorex C18, 10 mum, 125×30 mm, solvent: acetonitrile/0.05% formic acid gradient; (0 to 3 min. 10% acetonitrile to 35 min. 90% acetonitrile and a further 3 min. 90% acetonitrile)), and 11.4 mg (6.8% of theory, 99% purity) of the title compound from Example 210 were obtained. Example 207 N-[(1R)-1-(2-Chlorophenyl)-2,2,2-trifluoroethyl]-1-(2,4-difluorophenyl)-7-[3-hydroxy-2-oxopiperidin-1-yl]-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide (diastereomer 1, enantiomer A) 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=11.29 (d, 1H), 8.88 (s, 1H), 8.70 (d, 1H), 8.18-8.11 (m, 1H), 7.92-7.77 (m, 1H), 7.67-7.48 (m, 5H), 7.40-7.31 (m, 1H), 6.53-6.43 (m,…

19365-08-3, 19365-08-3 3-Hydroxypiperidin-2-one 264990, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Bayer Pharma Aktiengesellschaft; TELLER, Henrik; STRAUB, Alexander; BRECHMANN, Markus; MUeLLER, Thomas; MEININGHAUS, Mark; NOWAK-REPPEL, Katrin; TINEL, Hanna; MUeNTER, Klaus; FLIEGNER, Daniela; MONDRITZKI, Thomas; BOULTADAKIS ARAPINIS, Melissa; MARQUARDT, Tobias; VAKALOPOULOS, Alexandros; REBSTOCK, Anne-Sophie; WITTWER, Matthias Beat; (342 pag.)US2018/297994; (2018); 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, General procedure: To an oven-dried round-bottom flask with a stir bar were charged with a solution of secondary amines 2 (1.5 mmol) in 1 mLdry THF at room temperature under an argon atmosphere. To thissolution was slowly added 1.2 mL nBuLi (2.5 mol/L in n-hexane,3.0 mmol) via syringe. After stirring at 25 C for 10 min, a solution of fluoroarene 1 (1.0 mmol) in 1mL dry THF was added to the reaction flask. The reaction mixture was stirred for 0.5 h at 25 C, and then quenched with 2 mL saturated aqueous solution of NaCl and extracted with H2O (20 mL) and ethyl acetate (3 20 mL). The organic layer was separated and dried with anhydrous Na2SO4, filtered, and evaporated under vacuum. The crude product was purified by column chromatography on silica gel using a petroleum ether/ethyl acetate mixture as eluent to afford the pure target compounds.

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

Reference：
Article; Lin, Yingyin; Li, Meng; Ji, Xinfei; Wu, Jingjing; Cao, Song; Tetrahedron; vol. 73; 11; (2017); p. 1466 – 1472;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1062580-52-2,(3R,4R)-1-Benzyl-N,4-dimethylpiperidin-3-amine dihydrochloride,as a common compound, the synthetic route is as follows.

20g of compound 5,13.3g of compound 4 is added to the 500ml reaction flask,Add 266 ml of purified water,Add pre-mixed potassium carbonate solution with stirring(20 g of potassium carbonate was dissolved in 40 ml of purified water) and heated to reflux.After stirring and refluxing for 10 hours, TLC detection was started until the reaction was completed.Cool down to 20 ~ 30 C, add 120ml dichloromethane and stir to extract.The mixture was allowed to stand, dried, filtered, and washed to obtain a reaction solution.Add n-heptane with stirring at room temperature.Decreasing to 0 to 10 C for 2 to 4 hours,Filter and wash. Drying at 50-60 C for 6 hours under vacuum to obtain compound 3,Weighing 20.9g,Yield: 82.3%, purity: 99.9%., 1062580-52-2

The synthetic route of 1062580-52-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Qilu Tianhe Huishi Pharmaceutical Co., Ltd.; Li Fadong; Wu Ke; Yang Qingkun; Li Zhuohua; Zhou Xianfeng; Pan Guangpeng; (7 pag.)CN108276414; (2018); A;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

710972-40-0, tert-Butyl 4-((2-methoxyethyl)amino)piperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

710972-40-0, 137 N-(l-[2-(lH-Indazol-4-ylV4-mophiholin-4-yl-thienor3,2-d1pyrimidin-6- ylmethvH-piperidin-4-vU-N-(2-methoxy-ethyl)-methanesulfonarnide. EPO Via N- [ 1 -(2-chloro-4-mophiholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)- piperidin-4-yl]-N-(2-methoxy-ethyl)-methanesulfonamide, prepared from N-(2- methoxy-ethyl)-N-piperidin-4-yl-methanesulfonamide.Amine preparation: To a solution of 4-(2-methoxyethylamine)-piperidine-l- carboxylic acid tert-butyl ester (see preparation of 121) (0.50g) in DCM (1OmL) was added triethylamine (0.3OmL) followed by methanesulfonyl chloride (0.16mL). After stirring for 4 h the reaction mixture was then diluted with DCM, washed with sodium bicarbonate solution, dried (MgSO4) and the solvent removed in vacuo. The residue was purified by flash chromatography to yield 4-[methanesulfonyl-(2-methoxy- ethyl)-amino]-piperidine-l -carboxylic acid tert-bxxy ester (0.474g). Treatment of this compound with HCl in DCM/MeOH yielded the desired amine, which was isolated as the hydrochloride salt.1H NMR (400MHz, CDCl3) 1.78 (2H, m), 1.92 (2H, m), 2.21 (2H, t, J=10.9Hz), 2.90 (3H, s), 3.07 (2H, br d, J=I 1.6Hz), 3.38 (5H, m), 3.54 (2H, t, J=6.3Hz), 3.68 (IH, m), 8.83 (2H, s), 3.94 (4H, m), 4.10 (4H, m), 7.38 (IH, s), 7.50 (IH, t,J=7.7Hz), 7.60 (IH, d, J=8.2Hz), 8.29 (IH, d, J=7.1Hz), 9.02 (IH, s), 10.10(1H, br s); MS (ESI+) 586 (MH+).

The synthetic route of 710972-40-0 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; PIRAMED LIMITED; WO2006/46031; (2006); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

122860-33-7, Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

122860-33-7, Example 3; 4-Formyl-piperidine-1-carboxylic acid benzyl ester (3); Oxalyl chloride (59.1 ml_, 674 mmol) was dissolved in dichloromethane (500 ml_) and cooled to -78C. Dimethylsulfoxide (68.3 ml_, 963 mmol) was added and the mixture was stirred for 15 min. 4-Hydroxymethyl-piperidine-1-carboxylic acid benzyl ester (2) (120 g, 481 mmol) dissolved in dichloromethane (500 ml_) was added. The mixture was allowed to warm to -55C for 15 min. The mixture was again cooled to -78C and triethylamine (205 ml_, 1443 mmol) in dichloromethane (250 ml_) was added. The suspension was allowed to warm to room temperature and quenched with glacial acetic acid (100 ml_). The solution was washed with water and the aqueous phase extracted with dichloromethane (2 x 200 ml_). The combined organic layers were washed with brine, dried over sodium sulphate, filtered and concentrated to give 4- formyl-piperidine-1-carboxylic acid benzyl ester (119 g, 100%).

As the paragraph descriping shows that 122860-33-7 is playing an increasingly important role.

Reference：
Patent; NEUROSEARCH A/S; WO2007/93603; (2007); 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

[REFERENCE EXAMPLE]The procedures for synthesizing 2-(2,2,6,6-tetramethylpiperidinylmethyl)phenylboronic acid used as a catalyst (hereinafter, written as the catalyst C) will be described below. This compound is a known compound. [0023] First, a flask was loaded with 2-bromobenzyl bromide (10 mmol), potassium carbonate (22 mmol), potassium iodide (11 mmol), 3-pentanone (20 mL) and 2,2,6,6-tetramethylpiperidine (22 mmol). The mixture was heated under reflux for 2 days. After being allowed to cool to room temperature, the mixture was filtered to remove the insolubles. The filtrate was washed with water 2 times, and the aqueous phases were each extracted with chloroform. The organic phases were combined together, dried with sodium sulfate, and concentrated under reduced pressure. The resultant crude product was purified by column chromatography (NH silica gel, hexane), thereby obtaining the target amine compound, namely, 1-bromo-2-(2,2,6,6-tetramethylpiperidinylmethyl)benzene in 92% yield.

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

Reference：
Patent; National University Corporation Nagoya University; ISHIHARA, Kazuaki; SAKAKURA, Akira; EP2816026; (2014); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

5274-99-7, 1-Benzoylpiperidine-4-carboxylic acid is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5274-99-7, To a mixture of tert-butyl (3-{[(2R, 3S)-2-AMINO-3-(LH- indol-3-yl) butanoyl amino} benzyl) carbamate (0.20 g, 0.47 MMOL), and 1-benzoylpiperidine-4-carboxylic acid (0.12 g, 0.53 mmol), WSC (0.11 g, 0.58 mmol) and HOBt (0.088 g, 0.57 mmol) were added THF (1.0 ML) and acetonitrile (1.0 ML) at room temperature, and the mixture was stirred overnight. To the reaction solution were added saturated aqueous solution of sodium hydrogen carbonate and ethyl acetate and the mixture was subjected to extraction. The organic layer was filtered by passing through a silica gel layer, and concentrated under reduced pressure. The residue was dissolved in dioxane (1.0 mL), and 4N hydrochloric acid-dioxane solution (1.0 ML) was added at room temperature. The mixture was stirred for 30 min. To the reaction solution were added saturated aqueous solution of sodium hydrogen carbonate and a mixed solvent of ethyl acetate-dichloromethane and the mixture was subjected to extraction. The organic layer was dried (MGS04) and concentrated under reduced pressure. The residue was purified by HPLC (acetonitrile/water = 10/90-100/0, containing 0.1% trifluoroacetic acid). A fraction of the object product was concentrated and neutralized with saturated aqueous solution of sodium hydrogen carbonate to give the title compound (0.084 g, yield 33%). LC/MS (ESI) m/z 538 (M+H+).

As the paragraph descriping shows that 5274-99-7 is playing an increasingly important role.

Reference：
Patent; TAKEDA CHEMICAL INDUSTRIES, LTD.; WO2004/46107; (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.5166-67-6,Ethyl N-methylpiperidine-3-carboxylate,as a common compound, the synthetic route is as follows.

S -N-Boe -ethyl nlpeeotate (.) (0,7 g, 0.0041 mol) and aceiamide oxirne (0.75g, 0.0102 mol) were. dissolved in 30 mL teirahydrofuran. Sodium methoxide (l.lg, 0.0205 mol) was added and. the mixture was heated at reflux for 2 hours. The mixture was concentrated to remove THF and partitioned between water (25 mL) and dichloromethane ( I x 25 mL). The aqueous layer was extracted with an additional 2 x 25 mL dichioromethane. The combined organics were washed with I< 50 mL saturated, sodium chloride, and dried over Nag&O . The dried organics were evaporated to an oil. The residue was chromatogra;phed with 5 g silica gel, 5% raethano./ethyl acetate, to obtain 0.51 g of the tree base. Hydrochloric acid in ethanol (2.5 M) (1.6 mL, 0.01 1 mol) was added and the mixture was concentrated to dryness. Crystallization fromethanol/ 'IBE fforded 436 mg white solid. MB (ESI) mlz 182 [ +B]. hi NM (DMSO-46) 5 1.59-1.66 (m, I H), 1.8.8.- 1.98 (s, 2 H), 2.17-2.20 (d, 1H), 234 (s, 3 H), 2.77 (s, 3 H), 2.92- 2.95 (m, 1 H), 3.18-3.21 (m, 1 H% 337-3.47, (d, 1H), 3.60-3.78, (m, 2H). 5166-67-6, The synthetic route of 5166-67-6 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; MITHRIDION, INC.; ABRAHAM, Brent, D.; COPP, Richard, R.; FARNHAM, James, G.; HANSON, Seth, A.; HENDRICKSON, Michael, L.; OCKULY, Jeffrey, C.; TWOSE, Trevor, M.; VERDONE, Melinda, L.; WO2012/33956; (2012); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem