Tag: M.W:200-300

188869-05-8, tert-Butyl 3-bromo-4-oxopiperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

188869-05-8, [0427] A mixture of 5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile (1.5 g, 5.4mmol) and K2C03 (2.24 g, 16.3 mmol) in 50 mL of DMF at 80 DC was stirred under N2 for 45min before tert-butyl3-bromo-4-oxopiperidine-1-carboxylate (4.5 g, 16.3 mmol) was added inone portion. Then the mixture was stirred at 80 DC for 1 hr. After cooling down toRT, 150 mLof water and 150 mL of EA was added. Aqueous phase was further extracted with EA (1 00 mL x 3). The combined organic layers were washed with brine, dried over Na2S04 and concentratedto get crude product which was chromatographed on I5 g of silica gel using DCM/MeOH (40011to 20011) as eluant to afford 850 mg (35%) oftert-butyl3-cyano-2-(4-phenoxyphenyl)-5,6-dihydro -4H -pyrazolo[5′, I’ :2,3 ]imidazo[ 4,5-c ]pyridine-? (8H)-carboxylate as an off-white solid.MS (ESI) m/e [M+ It 455.9.

The synthetic route of 188869-05-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GUO, Yunhang; BEIGENE, LTD.; WANG, Zhiwei; WO2014/173289; (2014); A1;,
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143900-44-1, (S)-tert-Butyl 3-hydroxypiperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 57[0363] Synthesis of (^)-l-(3-(7H-pyrrolo[2,3-J]pyrirnidin-4-yloxy)piperidin- chloro-5-fluorophenylamino)ethanone.Reagents and conditions: a) NaH, DMSO, 4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H- pyrrolo[2,3-J]pyrimidine; b) TBAF, THF, reflux, 5 h; c) HC1 in 1 ,4-dioxane, rt, 30 min; d) EDCI, HOBt, 2-(3-chloro-5-fluorophenylamino)acetic acid, DMF, rt, 24 h.[0364] Synthesis of (S^-tert-butyl 3-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H- pyrrolo[2,3-J]pyrimidin-4-yloxy)piperidine-l-carboxylate: To a solution of (^-ieri-butyl 3- hydroxypiperidine-l-carboxylate (0.4 g, 2.0 mmol) in DMSO (5 mL) under nitrogen, was added NaH (60% suspension in mineral oil, 79 mg, 2.0 mmol). After the reaction was stirred for 1.5 h at rt, a solution of 4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-J]pyrimidine (564 mg, 2.0 mmol) in DMSO (5 mL) was added dropwise at rt and the mixture was heated at 50 C for 2h. The reaction mixture was cooled to rt, diluted with water (10 mL) and extracted with EtOAc (4 x 60 mL). The combined organic layer was washed with water (50 mL), dried over Na2S04 and concentrated in vacuo to give the crude compound which was purified by column chromatography (silica gel, gradient EtOAc in Hexanes) to give (750 mg, 85%) of the titled intermediate., 143900-44-1

As the paragraph descriping shows that 143900-44-1 is playing an increasingly important role.

Reference£º
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian, T.; SCOTT, Daniel; CONLON, Patrick; JENKINS, Tracy, J.; POWELL, Noel; GUAN, Bing; CURERVO, Julio, H.; WANG, Deping; TAVERAS, Art; WO2012/58645; (2012); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.28697-07-6,N-Cbz-2-Piperidinecarboxylic acid,as a common compound, the synthetic route is as follows.

General procedure: (i) A solution of 2,6-difluorobenzoic acid (0.32 mol) in thionyl chloride (100 mL) was heated to reflux for 2 h. The resulting solution was concentrated and acid chloride intermediate was used in the next step without additional purification. To a solution of the acid chloride in anhydrous THF (100 mL) was added ammonium hydroxide (79 mL) at 0 C. After stirring at room temperature for 0.5 h, the reaction mixture was concentrated under reduced pressure. Then the reaction mixture was poured into cooled water (50 mL), extracted with ethyl acetate (100 mL x 3), and washed with brine (150 mL x 2). The organic layer was dried and concentrated to give the intermediate 2 in 90% yield which used in next step without purification. (ii) To a solution of 2,6-difluorobenzamide (0.28 mol) in concentrated sulfuric acid (90 mL) was added fuming nitric acid (12 mL) by dropwise under 0 C. The mixture was stirred for 2 h at room temperature. The pH was adjusted to 6 with 30% sodium hydroxide solution, then filtered and the filtrate was extracted with ethyl acetate (100 mL x 3),and washed with brine (150 mL x 2). The organic layer was dried and concentrated in vacuo to give the intermediate 3 as yellow solid in 91.40%yield. (iii) To a solution of 2,6-difluoro-3-nitrobenzamide (0.25 mol) in ethanol (300 mL) was added ammonium hydroxide (25 mL). The reaction mixture was stirred at room temperature overnight and the precipitate was collected by filtration, washed with isopropanol and dried in vacuum to give 4 31.5 g as yellow solid, yield 77.6%. (iv) A suspension of 2-amino-6-fluoro-3-nitrobenzamide (0.05 mol) in ethanol (100 mL) was reduced by hydrogen in the presence of palladium on carbon (10%, 1.00 g). After stirring at room temperature for 12 h, the reaction mixture was filtered. Solvent was removed under reduced pressure and the residue was subjected to silica gel column chromatography using dichloromethane/methanol (3:1) as eluent to give 55.00 g as light yellow solid, yield 58.9%. (v) To a solution of 3-pipecolinic acid (0.06 mol) and 2,3-diamino-6-fluorobenzamide (0.06 mol) in DMF (100 mL) was treated with PyBOP (0.06 mol) and N,N-diisopropylethylamine (0.18 mol).The reaction mixture was stirred at room temperature overnight. The solvent was removed using high vacuum. The residue was subjected to flash column chromatography using methylene chloride/methanol (30:1) to give the intermediate 6 as a white solid. The intermediate 6 was dissolved in glacial acetic acid (30 mL) and refluxed for 4 h until the reaction was complete (monitoring by TLC). The solvent was removed and the solid residue was purified by column chromatography using methylene chloride/methanol(80:1) as eluent to give pure 7a-7e in 50-72% yield. (vi) A solution of 7a-7e (25 mmol) in methanol (100 mL) was reduced with hydrogen in the presence of palladium on carbon (10%, 1.00 g). After stirring at room temperature for 12 h, the reaction mixture was filtered, and the filtrate was concentrated to give pure target compounds 8a-8e in 52-80% yield., 28697-07-6

The synthetic route of 28697-07-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Wang, Junwei; Wang, Xuyan; Li, Hui; Ji, Dezhong; Li, Yuyan; Xu, Yungen; Zhu, Qihua; Bioorganic and Medicinal Chemistry Letters; vol. 26; 16; (2016); p. 4127 – 4132;,
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175213-46-4, N-Boc-Piperidin-4-yl-acetic acid methyl ester is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a -78 C. solution of 2-bromopyridine (1.86 ml, 19.5 mmol) in anhydrous THF (30 ml) was slowly added 1.6 M BuLi soln. in hexanes (10.8 ml, 17.3 mmol), resulting in a dark orange solution. The reaction mixture was allowed to stir for 90 min. at -78 C. The cold reaction mixture was cannulated over a period of 2 h into a -78 C. solution of 76 (2.5 g (9.72 mmol) in anhydrous THF (20 ml). The reaction mixture was allowed to stir for 2.5 h at -78 C., then was allowed to reach rt. The reaction mixture was quenched with AcOH, followed by extraction with CH2Cl2 (3¡Á70 ml). The organic layer was dried over Na2SO4, followed by concentration and flash chromatography (from 50% hexanes/CH2Cl2 to 10% acetone/CH2Cl2) to afford 0.41 g (2.83 g; 14%) of 77 as a yellow oil

175213-46-4, The synthetic route of 175213-46-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Schering Corporation; US2007/10513; (2007); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.175213-46-4,N-Boc-Piperidin-4-yl-acetic acid methyl ester,as a common compound, the synthetic route is as follows.

Diisopropylamine (3.40 mL, 24.2 mmol) was dissolved in tetrahydrofuran (70 mL). The mixture was cooled to -78 C. Butyllithium (2 M in cyclohexane, 12.2 muL, 24.4 mmol) was added dropwise to the reaction. The mixture was held at -78 C. with stirring and held for 20 minutes. A solution of tert-butyl 4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate (5.20 g, 20.2 mmol) in tetrahydrofuran (15 mL) was added to the mixture dropwise. The mixture was held at -78 C. with stirring and held for 45 min. In a separate flask, sodium hydride (60% in mineral oil, 970 mg, 24.3 mmol) was washed with hexanes then suspended in tetrahydrofuran (50 mL). The mixture was cooled to 0 C. A solution of N-(2-Fluoro-6-formylphenyl)pivalamide (4.50 g, 20.2 mmol) in tetrahydrofuran (20 mL) was added to the mixture dropwise. The mixture was held at 0 C. with stirring and held for 1 h. The above prepared aldehyde mixture was added to the ester mixture dropwise over 1.25 h. The mixture was held at -78 C. with stirring and held for 1 h. The reaction was quenched with aqueous ammonium chloride, warmed to room temperature, and diluted with water. The mixture was extracted ethyl acetate (2¡Á) and the aqueous phase was discarded. The material was dried (magnesium sulfate), filtered, and concentrated to dryness. Silica gel chromatography gave the title compound as white foam in 81% yield. Mass spec.: 381.2 (M-C4H8O2+H)+.

175213-46-4, The synthetic route of 175213-46-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Degnan, Andrew P.; Han, Xiaojun; Dubowchik, Gene M.; Macor, John E.; Mercer, Stephen E.; US2005/215576; (2005); A1;,
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15883-20-2, N-(2′,6′-Dimethylphenyl)-2-piperidinecarboxamide is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 7 A clean and dry four neck round bottom flask was charged with N-((R)-1- phenylethyl)phthalamic acid (28.9 gm), isopropanol (300 ml) and 2′,6′-pipecoloxylidide (25 gm). The reaction mixture was stirred at 25C to 30C for one hour. The reaction mass was cooled to 1 0C to 15C to get a precipitate of corresponding (R)-(-)- 2′, 6′- pipecoloxylidide-phthalamic acid salt (27.30 gm) which was separated by filtration to afford white crystalline solid. IR:- 3300.8, 3032.8, 1677.2, 1629.7, 1583.4, 1529.8, 1444.7, 1378.4, 1244.8, 1037.7, 947.9, 835.5, 699.9 CM”1 NMR:- delta = 1.39(d, J= 4.0Hz, 3H), 1.50-1.70(m, 4H), 2.13(s, 7H), 2.82(dd, J= 2.8Hz, 5.8Hz, 16.4Hz, 1H), 3.13(d, J = 12.4Hz, 1H), 3.79(dd, J = 2.8Hz, 2.8Hz, 1 1.0Hz, 1H), 5.06(pen, 1H), 7.04-7.10(m, 3H), 7.21(t, J= 7.2Hz, 7.2Hz, 1H), 7.3 l(t, J= 7.6Hz, 7.6Hz, 2H), 7.30-7.43(m, 4H), 7.57(d, J= 6.4Hz, 2H), 9.68(s, 1H), 10.27(s, 1H). The filtrate was concentrated under vacuum, treated with 10%) sodium carbonate (500 ml) and stirred the reaction mass at room temperature for 1.5 hours to get a solid. The solid was collected by filtration, washed with water and dried to get (S)-2′,6′-pipecoloxylidide. Yield – 12 gm (96%) Enantiomeric purity – 96.66% (R)-(-)-2′,6′-pipecoloxylidide-phthalamic acid salt was hydro lyzed with 10% sodium carbonate (520 ml) and stirred the reaction mass at room temperature for one hour to get a solid. The solid washed with water and dried to get (R)-2′,6′-pipecoloxylidide. Yield – 9.3 gm (74.4%) Enantiomeric purity – 95.95%

15883-20-2, As the paragraph descriping shows that 15883-20-2 is playing an increasingly important role.

Reference£º
Patent; NEON LABORATORIES LIMITED; DALVI, Mahesh Bhagoji; KENNY, Rajesh Shashikant; TARADE, Pradeep Kisan; WO2014/9964; (2014); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.79421-45-7,1-(4-Nitrophenyl)piperidin-4-ol,as a common compound, the synthetic route is as follows.

79421-45-7, A mixture of the yellowish solid (0.90 g, 4.05 mmol) and Pd-C (10%, 120 mg) in MeOH (20 mL) containing aqueous 6N HCl (0.20 mL) was hydrogenated under balloon H2 overnight. It was filtered through celite. The filtrate was concentrated in vacuo to give a solid (0.841 g) as l-(4-aminophenyl)piperidin-4-ol.

79421-45-7 1-(4-Nitrophenyl)piperidin-4-ol 613768, apiperidines compound, is more and more widely used in various fields.

Reference£º
Patent; PORTOLA PHARMACEUTICALS, INC.; WO2009/131687; (2009); A2;,
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84163-13-3,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.84163-13-3,6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride,as a common compound, the synthetic route is as follows.

General procedure: To Boc-Xaa-OH (0.005 mol) and HOBt (0.765 g, 0.005 mol) dissolved in DMF (10 mL/g of peptide) and cooled to 0 C was added NMM (0.55 mL, 0.005 mol). EDCI (0.956 g, 0.005 mol) was added under stirring while maintaining the temperature at 0 C. The reaction mixture was stirred for an additional 10 min and pre-cooled solution of [3-(4-piperidinyl)-6-fluoro-1,2-benzisoxazole]HCl (1.285 g, 0.005 mol) and NMM (0.55 mL, 0.005 mol) in DMF (13 mL) was added slowly (Scheme 4). After 20 min, pH of the solution was adjusted to 8 by the addition of NMM and the reaction mixture was stirred overnight at room temperature. DMF was removed under reduced pressure and the residue was poured into about 200 mL ice-cold 90% saturated KHCO3 solution and stirred for 30 min. The precipitated product was taken into CHCl3 and washed with 5% NaHCO3 solution (2 ¡Á 20 mL), water (2 ¡Á 20 mL), 0.1 N cold HCl solution (2 ¡Á 20 mL) and finally brine solution (2 ¡Á 20 mL). The CHCl3 layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The products so obtained were recrystallized from ether/petroleum ether to get white colored desired conjugates (16-25).

84163-13-3 6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride 11334359, apiperidines compound, is more and more widely used in various fields.

Reference£º
Article; Suhas; Chandrashekar; Gowda, D. Channe; European Journal of Medicinal Chemistry; vol. 46; 2; (2011); p. 704 – 711;,
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309962-63-8, (S)-tert-Butyl methyl(piperidin-3-yl)carbamate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 4-(6-fluoropyridin-3-yl)-6-(l-methyl-lH-pyrazol-4-yl)pyrazolo[l,5 a]pyrazine-3-carbonitrile (Intermediate P7; 0.100 g, 0.313 mmol) in DMSO (6.26 mL) was treated with (S)-tert-butyl methyl(piperidin-3-yl)carbamate (0.268 g, 1.25 mmol) and K2CCb(s) (0.173 g, 1.25 mmol) and stirred overnight at 110 C. After cooling to ambient temperature, the reaction mixture was diluted with water (10 mL) and extracted with DCM (4 x 10 mL) in a PS Frit. The combined organic extracts were concentrated in vacuo, and purified by C18 reverse phase chromatography (using 0-60% ACN/water as the gradient eluent) to afford the title compound (106 mg, 66% yield). MS (apci) m/z = 514.2 (M+H).

309962-63-8, 309962-63-8 (S)-tert-Butyl methyl(piperidin-3-yl)carbamate 28875358, apiperidines compound, is more and more widely used in various fields.

Reference£º
Patent; ANDREWS, Steven W.; BLAKE, James F.; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MORENO, David A.; REN, Li; WALLS, Shane M.; (421 pag.)WO2018/136661; (2018); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.871022-62-7,tert-Butyl ((4-fluoropiperidin-4-yl)methyl)carbamate,as a common compound, the synthetic route is as follows.

The mixture of tert-butyl N-[(4-fluoro-4- piperidyl)methyl]carbamate (150.00 mg, 645.74 //mol, 1.00 eq) and 9H-fluoren-9-ylmethyl carbonochloridate (250.58 mg, 968.61 //mol, 1.50 eq) were dissolved in THF (20.00 mP) and H20 (4.00 mP), to which NaHCCp (162.75 mg, 1.94 mmol, 75.35 //F, 3.00 eq) was added in one portion. The resulting mixture was then stirred at 15 C for 14 h. The reacting solution was diluted with water (50 mP) and extracted with EA (50 mP x 3). The combined organic layers were concentrated under reduced pressure. The residue was purified by silica gel chromatography (pure PE to PE:EA = 5:1) to afford 9H-fluoren-9-ylmethyl 4-[(tert- butoxycarbonylamino)methyl]-4-fluoro-piperidine-l -carboxylate (163.00 mg, 358.61 //mol, 55.54% yield) as an off-white solid. The product was confirmed by PC-MS and used directly for the next step without further purification, 871022-62-7

871022-62-7 tert-Butyl ((4-fluoropiperidin-4-yl)methyl)carbamate 53415226, apiperidines compound, is more and more widely used in various fields.

Reference£º
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; (475 pag.)WO2020/41406; (2020); A1;,
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