Day: March 24, 2022

1039741-54-2, 1-Benzyl-3,3-difluoropiperidin-4-one is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Di-tert-butyl dicarbonate (1.19 g, 5.44 mmol) was added to a solution of i-benzyl-3,3-difluoropiperidin-4-one (995mg, 4.42 mmol) in EtCH (60 mL) under nitrogen.Palladium hydroxide (Pd 20% on carbon, 148 mg, 1.05mmol) was added and the system was evacuated andflushed with hydrogen several times. The mixture was stirred at RT for 20 h under hydrogen. The residual hydrogen was removed and the mixture was filtered over Celite, and washed with EtCH. Purification gave titled compound (810 mg, 3.44 mmol, 78% yield) as a white solid.1H NMR (400 MHz, DMSC-d6, ): 3.66-3.52 (m, 2H), 3.39-3.33 (m, 2H), 1.69-i .64 (m, 2H), 1.38 (5, 9H)

1039741-54-2, 1039741-54-2 1-Benzyl-3,3-difluoropiperidin-4-one 49761227, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; REDX PHARMA PLC; GUISOT, Nicolas; (266 pag.)WO2017/103611; (2017); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

3612-20-2, 1-Benzylpiperidin-4-one is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 294.14 g 1-benzylpiperidin-4-one in 2.1 L methanol was added to a solution of 448 g ammonium carbonate in 2.1 L hot water. The yellow turbid reaction mixture was cooled with an ice bath. A solution of 77 g sodium cyanide in 200 ml water was added dropwise over 10 min (exothermic.). After the addition the ice bath was removed and the reaction mixture was stirred at ambient temperature for 3 days. The resulting precipitate was filtered, washed with water (3x) and dried in a vacuum oven at 50C to obtain the intermediate 1.38.Yield: quantitative, 3612-20-2

The synthetic route of 3612-20-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; DAHMANN, Georg; FIEGEN, Dennis; FLECK, Martin; HOFFMANN, Matthias; KLICIC, Jasna; EAST, Stephen, Peter; NAPIER, Spencer, Charles, R.; SCOTT, John; WO2012/101013; (2012); 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.888952-55-4,Methyl 1-Boc-3-methylpiperidine-3-carboxylate,as a common compound, the synthetic route is as follows.

Step 2. 1-tert-Butyl 3-methyl 3-methylpiperidine-1,3-dicarboxylate. To a solution of 1-tert-butyl 3-methyl 3-methylpiperidine-1,3-dicarboxylate (15.86 g, 0.062 mol) in THF (100 ml) and H2O (10 ml) was added LiOH.H2O (7.76 g, 0.186 mol) at room temperature. The mixture was refluxed at 70 C. for 6 h. After TLC (Petroleum ether/EtOAc, 4:1, stained by iodine) showed the starting material to be consumed, the mixture was concentrated to dryness. The residue was diluted with H2O (300 mL) and then extracted with MTBE (100 mL×2). The organic layers were discarded. The resulting aqueous layer was acidified to pH 1 with 1M HCl (aq.) and then extracted with MTBE twice. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated to dryness to give 1-tert-butyl 3-methyl 3-methylpiperidine-1,3-dicarboxylate (13.97 g, 93%) as a white solid., 888952-55-4

888952-55-4 Methyl 1-Boc-3-methylpiperidine-3-carboxylate 46911995, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Thorarensen, Atli; Brown, Matthew Frank; Casimiro-Garcia, Agustin; Che, Ye; Coe, Jotham Wadsworth; Flanagan, Mark Edward; Gilbert, Adam Matthew; Hayward, Matthew Merrill; Langille, Jonathan David; Montgomery, Justin Ian; Telliez, Jean-Baptiste; Unwalla, Rayomand Jal; US2015/158864; (2015); 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.90802-45-2,3-Aminopiperidine-2,6-dione hydrobromide,as a common compound, the synthetic route is as follows.

Add 55.0 g (0.263 mol) of 3-amino-2,6-piperidinone hydrobromide to a 1000 ml reaction flask.Triethylamine 75ml, 200ml acetonitrile, stirred and mixed at room temperature, heated to 80 C, adding a mixture of 72.1g (0.263mol) of methyl 2-bromomethyl-3-nitrobenzoate and 150ml of acetonitrile, heat preservation reaction for 10h, Cold to room temperature,Slowly add 200ml of water and stir for 0.5h.The product was obtained as an off-white solid, 49.6 g, yield 65.2%.

90802-45-2, The synthetic route of 90802-45-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Shijiazhuang Duen Pharmaceutical Technology Co., Ltd.; Fang Yu; Du Yumin; (8 pag.)CN109776493; (2019); A;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

1000931-04-3, 1-Boc-3-Hydroxy-4-phenylpiperidine is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(j) A solution of 4.0 g tert-butyl (13.8 mmol) of tert-butyl (3RS,4RS)-3-hydroxy-4-phenyl-piperidine-1-carboxylate in 100 ml of methanol was hydrogenated at 150 bar at 100 C. for 18 hours using a rhodium(5%)-aluminium oxide catalyst. For the working up, the catalyst was filtered off, washed with methanol and the solution obtained was evaporated under reduced pressure. For purification, the residue was chromatographed on silica gel using a 4:1 mixture of hexane and ethyl acetate as the eluent. There were obtained 2.32 g (59% of theory) of tert-butyl (3RS,4RS)-4-cyclohexyl-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate as a colourless solid; MS: 283 (M)+., 1000931-04-3

As the paragraph descriping shows that 1000931-04-3 is playing an increasingly important role.

Reference：
Patent; Hoffmann-La Roche Inc.; US6051712; (2000); A;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19365-08-3,3-Hydroxypiperidin-2-one,as a common compound, the synthetic route is as follows.

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 (283 mumol) of the compound from Example 80A were reacted with 39.1 mg (340 mumol) of rac-3-hydroxypiperidin-2-one in the presence of 58.7 mg (425 mumol) of potassium carbonate, 13 mg (57 mumol) of palladium(II) acetate and 33 mg (57 mumol) of Xantphos in 2.5 ml of dioxane. The crude product was purified by means of preparative HPLC (column: Chromatorex C18, 10 mum, 125*40 mm, solvent: acetonitrile/0.1% formic acid gradient; (0 to 3 min. 10% acetonitrile to 40 min. 90% acetonitrile and a further 3 min. 90% acetonitrile), and 102 mg (59% of theory, 100% purity) of the title compound were obtained. 1H NMR (400 MHz, DMSO-d6) delta [ppm]=11.34 (br. d, 1H), 8.89 (s, 1H), 8.70 (d, 1H), 8.17-8.09 (m, 1H), 7.94-7.75 (m, 1H), 7.68-7.56 (m, 2H), 7.41-7.27 (m, 3H), 6.51-6.39 (m, 1H), 5.52-5.46 (m, 1H), 4.27-4.17 (m, 1H), 3.71-3.58 (m, 1H), 3.54-3.40 (m, 1H), 2.12-2.01 (m, 1H), 1.86-1.71 (m, 1H), 1.71-1.57 (m, 1H). LC-MS (Method 3): Rt=2.11 min; 609 [M+H]+. 91.2 mg of the title compound (racemic diastereomer mixture) were separated into the enantiomeric diastereomers by chiral HPLC (preparative HPLC: column: Daicel Chiralpak AZ-H 5 mum 250×30 mm; eluent: 50% isohexane, 20% ethanol; temperature: 25 C.; flow rate: 50 ml/min; UV detection: 220 nm). This gave (in the sequence of elution from the column) 17.8 mg of diastereomer 1 (96.5% de) Rt=3.19 min, 14.5 mg (95% de) of diastereomer 2 Rt=4.21 min, 17.4 mg (97% de) of diastereomer 3 Rt=6.11 min, and 14.5 mg (97% de) of diastereomer 4 Rt=10.80 min. [Analytical HPLC: column: Daicel AZ-3 3 mum 50×4.6 mm; eluent: 50% isohexane, 50% ethanol; temperature: 30 C.; flow rate: 1 ml/min; UV detection: 220 nm] Example 248 1-(2,4-Difluorophenyl)-N-[1-(2,6-difluorophenyl)-2,2,2-trifluoroethyl]-7-[3-hydroxy-2-oxopiperidin-1-yl]-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide (diastereomer 1) 1H NMR (400 MHz, DMSO-d6) delta [ppm]=11.34 (br. d, 1H), 8.89 (s, 1H), 8.70 (d, 1H), 8.17-8.10 (m, 1H), 7.93-7.76 (m, 1H), 7.68-7.57 (m, 2H), 7.40-7.27 (m, 3H), 6.51-6.39 (m, 1H), 5.52-5.46 (m, 1H), 4.27-4.18 (m, 1H), 3.71-3.59 (m, 1H), 3.54-3.41 (m, 1H), 2.12-2.01 (m, 1H), 1.83-1.73 (m, 2H), 1.71-1.58 (m, 1H). LC-MS (Method 3): Rt=2.12 min; 609 [M+H]+. Example 249 1-(2,4-Difluorophenyl)-N-[1-(2,6-difluorophenyl)-2,2,2-trifluoroethyl]-7-[3-hydroxy-2-oxopiperidin-1-yl]-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide (diastereomer 2) 1H NMR (400 MHz, DMSO-d6) delta [ppm]=11.37-11.31 (m, 1H), 8.89 (s, 1H), 8.70 (d, 1H), 8.13 (dd, 1H), 7.94-7.75 (m, 1H), 7.68-7.56 (m, 2H), 7.41-7.26 (m, 3H), 6.51-6.38 (m, 1H), 5.52-5.46 (m, 1H), 4.27-4.16 (m, 1H), 3.72-3.58 (m, 1H), 3.53-3.39 (m, 1H), 2.12-2.01 (m, 1H), 1.83-1.73 (m, 2H), 1.72-1.57 (m, 1H). LC-MS (Method 3): Rt=2.13 min; 609 [M+H]+. Example 250 1-(2,4-Difluorophenyl)-N-[1-(2,6-difluorophenyl)-2,2,2-trifluoroethyl]-7-[3-hydroxy-2-oxopiperidin-1-yl]-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide (3rd diastereomer) 1H NMR (400 MHz, DMSO-d6) delta [ppm]=11.37-11.31 (m, 1H), 8.89 (s, 1H), 8.70 (d, 1H), 8.13 (dd, 1H), 7.94-7.75 (m, 1H), 7.68-7.56 (m, 2H), 7.40-7.26 (m, 3H), 6.51-6.39 (m, 1H), 5.52-5.46 (m, 1H), 4.26-4.17 (m, 1H), 3.72-3.59 (m, 1H), 3.52-3.40 (m, 1H), 2.12-2.01 (m, 1H), 1.84-1.73 (m, 2H), 1.72-1.58 (m, 1H). LC-MS (Method 3): Rt=2.12 min; 609 [M+H]+. Example 251 1-(2,4-Difluorophenyl)-N-[1-(2,6-difluorophenyl)-2,2,2-trifluoroethyl]-7-[3-hydroxy-2-oxopiperidin-1-yl]-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide (4th diastereomer) 1H NMR (400 MHz, DMSO-d6) delta [ppm]=11.34 (br. d, 1H), 8.89 (s, 1H), 8.70 (d, 1H), 8.17-8.09 (m, 1H), 7.93-7.76 (m, 1H), 7.68-7.57 (m, 2H), 7.40-7.2…

19365-08-3, As the paragraph descriping shows that 19365-08-3 is playing an increasingly important role.

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.72551-53-2,Ethyl 1-benzylpiperidine-3-carboxylate,as a common compound, the synthetic route is as follows.

72551-53-2, General procedure: Each ethyl N-substituted nipecotate derivative/ethyl N-substitutedisonipecotate derivative (1 mol) in 30 mL ethanol and hydraziniumhydroxide (10 mol) were heated under microwave irradiation (130 C,300 W) or refluxed for 24-48 h in an oil bath. After completion of thereaction (TLC), ethanol was evaporated and the residue was extractedwith dichloromethane or diethyl ether. The solvent was evaporatedunder reduced pressure until an oily residue occured. Then n-hexanewas added to the residue to give the title compound as a white solid.The precipitated crystals were separated by filtration.

As the paragraph descriping shows that 72551-53-2 is playing an increasingly important role.

Reference：
Article; Parlar, Sulunay; Sayar, Gozde; Tarikogullari, Ayse Hande; Karadagli, Sumru Sozer; Alptuzun, Vildan; Erciyas, Ercin; Holzgrabe, Ulrike; Bioorganic Chemistry; vol. 87; (2019); p. 888 – 900;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.35856-62-3,Piperidine-1-sulfonyl chloride,as a common compound, the synthetic route is as follows.,35856-62-3

1-Methyl-4-(4-nitrophenoxy)piperidine (1.4793 g, 6.26 mmol) was dissolved in 60 mL of EtOH, then Pd/C (209 mg) was added and the mixture was stirred under H2 atmosphere at ambient pressure overnight. The catalyst was filtered off to afford 4-[(1-methylpiperidin-4- yl)oxy]aniline (1.2567 g, 97% yield) as a brown solid, which was used in the next step without further purification.

The synthetic route of 35856-62-3 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; PHARMACYCLICS LLC.; ATALLAH, Gordana, Babic; CHEN, Wei; JIA, Zhaozhong, J.; POZZAN, Alfonso; RAVEGLIA, Lucal, Francesco; ZANALETTI, Riccardo; (815 pag.)WO2016/196776; (2016); A2;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

21168-72-9, 2-(4-(Aminomethyl)piperidin-1-yl)ethanol is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To the solution of compound 2-(4-(aminomethyl)piperidin-1-yl)ethanol (150 mg, 0.95 mmol) and compound 6-chloro-3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazine (200 mg, 0.64 mmol) in 3 mL DMSO was added DIEA (0.3 mL, 1.37 mmol) and 10 mg CsF, the solvent was stirred for 5 h at 120 C., Then the mixture was purified by HPLC to afford the compound 2-(4-(((3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazin-6-yl)amino)methyl)cyclohexyl)ethanol (34 mg, 8.2%) as a brown solid. (0522) 1H-NMR (CDCl3/400 MHz): delta 8.61 (s, 1H), 8.20-8.25 (m, 1H), 7.95-8.05 (m, 2H), 7.66 (t, J=4.4 Hz, 1H), 7.21-7.28 (m, 1H), 3.80-3.90 (m, 2H), 3.62-3.75 (m, 2H), 3.37 (d, J=6.4 Hz, 2H), 3.21 (t, J=5.2 Hz, 2H), 2.91-3.09 (m, 2H), 2.10 (d, J=14.0 Hz, 2H), 1.51-1.69 (m, 2H). MS (ES+, m/z): (M+H)+: 435.5.

21168-72-9, 21168-72-9 2-(4-(Aminomethyl)piperidin-1-yl)ethanol 7330476, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Tolero Pharmaceuticals, Inc.; Xu, Yong; Brenning, Benjamin Gary; Kultgen, Steven G.; Liu, Xiaohui; Saunders, Michael; Ho, Koc-Kan; (119 pag.)US9416132; (2016); B2;,
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

(1.1.1 ) (S)-tert-butyl 3-((2-chloro-5-iodopyrimidin-4-ylamino)methyl)piperidine-1- carboxylate. To a stirred solution of 2,4-dichloro-5-iodopyrimidine (3.5 g, 12.73 mmol) in THF (50 ml.) at -700C was added dropwise a solution of (SS^aminomethyl-i-piperidinecarboxylic acid- 5 (1 ,1-dimethyl)ethyl ester (3.0 g, 14 mmol) and DIEA (2.88 mL, 16.55 mmol) in THF (50 ml_). The reaction mixture was allowed to warm up to room temperature overnight. Then, the reaction mixture was diluted with EtOAc and washed with saturated NH4CI solution (2x) and brine (1x). The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by column chromatography (SiO2, heptane/EtOAc; 10 100% heptane to 30% EtOAc as mobile phase) and the title compound was obtained as a white solid in 38% yield (2.19 g, 4.84 mmol). LC-MS: peak at 4.04 min., mass [M+H] = 453., 140645-24-5

As the paragraph descriping shows that 140645-24-5 is playing an increasingly important role.

Reference：
Patent; N.V. ORGANON; PHARMACOPEIA, LLC; WO2009/124965; (2009); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem