Heterocyclic Building Blocks-piperidine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19099-93-5,1-Cbz-Piperidin-4-one,as a common compound, the synthetic route is as follows.

To a -20 0C solution of N,N,N’,N’-tetraniethylethylenediamine (0.335 g, 2.89 mmol) in THF (1 mL) was added n-butyllithium (2.5M, 1.15 mL, 2.89 mmol) over 10 min. After 30 min, the mixture was cooled to -78 0C and tert-butyl (6-chloropyridin-2-yl)carbamate (0.300 g, 1.31 mmol) in THF (0.8 mL) was added over 15 min. After Ih, the reaction was warmed to -50 0C, stirred for 2h and then N-benxyloxycarbonyl-4-piperidinone (0.459 g, 1.97 mmol) in THF (1 mL) was added over 10 min. The reaction was allowed to warm to room temperature and then stirred for 24 h. A solution of saturated aqueous NaHCO3 was added and the mixture extracted with EtOAc (3x). The combined organic layers were washed with H2O, brine, dried over MgStheta4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of 25 to 50% ethyl acetate: hexane to give the title compound (0.160 g). MS: mlz = 338.0 (M + 1).

19099-93-5, 19099-93-5 1-Cbz-Piperidin-4-one 643496, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; MERCK & CO., INC.; WO2006/99268; (2006); A2;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.24686-78-0,1-Benzoylpiperidin-4-one,as a common compound, the synthetic route is as follows.

Method 1 Preparation of 3,4-Dihydro-spiro[(2H)-1-benzopyran-2,4′-piperidine]-4-one hydrochloride A solution of 2-acetylphenol (5 g, 0.037 mmol), 1-benzoyl-4-piperidone (7.5 g, 0.037 mmol), pyrrolidine (2.6 g, 0.037 mol) and CH3 OH (50 ml) was heated at reflux for 8 hours. After cooling to room temperature overnight, the solid was filtered to yield 8.2 g of 1′-benzoyl-3,4-dihydro-spiro[(2H)-1-benzopyran-2,4′-piperidin]-4-one. The mother liquor was concentrated to dryness and the residue triturated with ether to yield an additional 1.7 g (83percent total yield).

24686-78-0, The synthetic route of 24686-78-0 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Merck & Co., Inc.; US5206240; (1993); 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.21168-72-9,2-(4-(Aminomethyl)piperidin-1-yl)ethanol,as a common compound, the synthetic route is as follows.

(Z)-4-(((1 -Acetyl-6-(methoxycarbonyl)-5-methyl-2-oxoindolin-3-ylidene) (phenyl)methyl)ami no)benzoic acid, trifluoroacetate adduct (Intermediate E) (75 mg,0.128 mmol), and HATU (73 mg, 0.192 mmol) in DMF (2 mL) were stirred at rt for 10 mm thenHunig?s base (179 p1, 1.03 mmol) and 2-(4-(aminomethyl)piperidin-1-yl)ethanol (73.1 mg,0.462 mmol) were added. The mixture was stirred at rt for 3 h and piperidine (127 p1, 1.28mmol) was added. The mixture was stirred at rtfor 18 h. The reaction mixture was partitioned between DCM (25 mL) and saturated aqueous NaHCO3 solution (10 mL). The organic layer was washed with brine (10 mL) and the solvent was evaporated under reduced pressure. The crude product was loaded onto a column of SCX (2 g) in 5% AcOH in MeOH (10 mL). The column was washed with MeOH (10 mL) and the filtrte was discarded. Then the product waseluted with 1% ammonia in MeOH (25 mL). The solvent was evaporated under reduced pressure and the product was purified by flash column chromatography (Si02, 12 g, 0-30% MeOH in DCM, gradient el ution) to afford (Z)-methyl 3-(((4-(((1 -(2-hydroxyethyl)piperidin-4- yl)methyl)carbamoyl)phenyl)am ino)(phenyl) methylene)-5-methyl-2-oxoindoline-6-carboxylate as a light yellow solid (63 mg, 63%); Rt 1.56 mm (Method 1); mlz 569 (M+H) (ES); 1H NMRO: 1.05-1.19 (2H, overlapping m), 1.47 (1H, m), 1.58 (2H, m), 1.81-1.94 (2H, overlapping m), 2.13 (3H, s), 2.28-2.40 (2H, overlapping m), 2.82 (2H, m), 3.07 (2H, t), 3.46 (2H, m), 3.75 (3H, s), 4.34 (1H, s), 5.61 (1H, s), 6.86 (2H, m), 7.36 (1H, s), 7.52 (2H, m), 7.57-7.70 (5H, m), 8.32 (1H, t), 10.88 (1H, s), 12.23 (1H, s).

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; RESPIVERT LIMITED; WALTERS, Iain; BIRCH, Louise; COLLINGWOOD, Stephen, Paul; STEVENSON, Christopher, Scott; (110 pag.)WO2017/153748; (2017); A1;,
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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: 4-morpholinobenzaldehyde (1 mmol, 0.191 g) was added to a stirred mixture of malononitrile (1.5 mmol, 0.099 g), and catalytic amount of SSC NPs (0.012 g, 2 mol%) in ace-tonitrile (10 mL). It was allowed to the mixture to stir at 70 C under sonication about 25-60 minutes. After completion of the reaction (the reaction progress was monitored by TLC using EtOAc/n-hexane (1:1) as eluent), the reaction mixture was filtered to separate precipitate. Next, the pre-cipitate was dissolved in boiling ethanol and then was fil-trated to separate catalyst. Finally, pure crystalline product was obtained from filtrate. Since the catalyst is reusable, at the end of the reaction, it was washed by boiling methanol three times (3 × 2 mL), dried at 90 C for 2 h and re-used in further cycles. Also, in the following, we explain more details about reusability results of the catalyst on model reaction., 10338-57-5

The synthetic route of 10338-57-5 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Pourshojaei, Yaghoub; Nikzad, Maryam; Eskandari, Khalil; Darijani, Mohammad-Hossein; Hassanzadeh, Abdolreza; Faghih-Mirzaei, Ehsan; Asadipour, Ali; Croatica Chemica Acta; vol. 91; 1; (2018); p. 19 – 28;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

1075-89-4, 8-Azaspiro[4.5]decane-7,9-dione is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 3 A mixture of 5-hexen-1-ol (5 g) and 8-azaspiro[4.5]decane-7,9-dione (14 ml) in triethylamine (150 ml) was cooled on an ice bath. Methane-sulfonyl chloride (8.6 g) in triethylamine (50 ml) was added dropwise and the mixture was stirred at room temperature for 1 hour. The mixture was filtered off and the filtrate evaporated. Dichloromethane (7.7 g), potassium carbonate (7.6 g) and N,N-dimethylformamide (100 ml) were added to the residue and the mixture was stirred at 160 C. overnight. The mixture was filtered off and the filtrate evaporated. The residue was purified by short open column chromatography over silica gel (eluent: CH2 Cl2 /CH3 OH 100/0 to 98/2). The pure fractions were collected and evaporated, yielding 1.5 g (13%) of 8-(5-hexenyl)-8-azaspiro[4.5]decane-7,9-dione (interm. 8)., 1075-89-4

The synthetic route of 1075-89-4 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Janssen Pharmaceutica N.V.; US5552399; (1996); 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.61995-20-8,Benzyl 3-oxopiperidine-1-carboxylate,as a common compound, the synthetic route is as follows.,61995-20-8

A mixture of benzyl 3-oxopiperidine-l-carboxylate (25 g, 0.107 mmol, 1.0 ep), ethyl cyanoacetate (14.54 g, 0.129 mmol, 1.2 eq), NH4OAc (2.09 g, 0.026 mmol, 0.25 eq) and acetic acid (5 mL) in toluene (250 mL) was refluxed at 130 C for 16 h. After the completion of reaction (TLC: Rf. 0.5 (30% ethyl acetate in hexane)), the reaction mixture was cooled to room temperature, quenched with a saturated aqueous solution of NaHC03 (500 mL) and extracted with EtOAc (2 x 300 mL). The combined organic layer was dried over Na2S04, filtered and concentrated under reduced pressure to afford crude product. The crude was purified by column chromatography (200-400 mesh silica-gel, eluent hexanes/EtOAc 90: 10 to 80:10,) to afford benzyl (?T)-3-(l-cyano-2-ethoxy-2- oxoethylidene)piperidine-l-carboxylate (24 g, yield: 68%) as a thick liquid. LCMS: 89%; *H NMR (400 MHz, DMSO-<) delta (ppm): 7.46 - 7.33 (m, 4H), 7.10 (d, / = 12.7 Hz, 1H), 5.19 - 5.15 (d, / = 13.4 Hz, 3H), 4.19 (dq, / = 14.2, 7.1 Hz, 2H), 3.59 - 3.50 (m, 2H), 2.10 (dt, / = 16.7, 6.3 Hz, 1H), 2.03 - 1.90 (m, 1H), 1.82 (d, / = 8.5 Hz, 2H), 1.22 (dq, / = 10.8, 6.1, 4.3 Hz, 4H). MS (ESI) m/z 329 [C18H20N2O4 + H] + As the paragraph descriping shows that 61995-20-8 is playing an increasingly important role. Reference：
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; NACRO, Kassoum; (223 pag.)WO2018/21977; (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.301225-58-1,tert-Butyl 4-(propylamino)piperidine-1-carboxylate,as a common compound, the synthetic route is as follows.

Step A 4-(N-(N-Benzylcarbamoyl)-N-(prop-1-yl)amino)-piperidine trifluoroacetate The title compound was prepared by the reaction of 4-(N-(prop-1-yl)amino)-1-tert-butoxycarbonylpiperidine (from Example 17, Step A) with benzyl isocyanate, followed by treatment of the product with 50% TFA in CH2Cl2 to remove the tert-butoxycarbonyl group, affording the title compound. ESI-MS: 276.1 (M+H)., 301225-58-1

The synthetic route of 301225-58-1 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Merck & Co., Inc.; US6399619; (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.1062580-52-2,(3R,4R)-1-Benzyl-N,4-dimethylpiperidin-3-amine dihydrochloride,as a common compound, the synthetic route is as follows.

A. Mix 10.0 kg of purified water, 2.6 kg of acetonitrile, 1.7 kg (3R, 4R) -1-benzyl-N, 4-dimethylpiperidine-3-amine dihydrochloride and 2.3 kg of potassium carbonate, and stir To dissolve B. Add 1.8 kg of 4-chloro-7-p-toluenesulfonyl-pyrrolo [2,3-d] pyrimidin-4-amine to the product obtained in the previous step several times, and raise the temperature to 75-85 C for 10 hours for reaction. HPLC detection; C. Reduce the temperature to 20-30 C and stir for 2 hours, suction filter, wash the filter cake with 3kg of purified water and set aside;, 1062580-52-2

1062580-52-2 (3R,4R)-1-Benzyl-N,4-dimethylpiperidin-3-amine dihydrochloride 45790119, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Jiangsu Haiyuekang Pharmaceutical Technology Co., Ltd.; Pei Xinyu; Chen Zeming; Xie Rongguang; (12 pag.)CN110668995; (2020); 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.885275-00-3,Benzyl 4-iodopiperidine-1-carboxylate,as a common compound, the synthetic route is as follows.,885275-00-3

A premixed mixture of TMSCl and 1,2-dibromoethane (7:5, v/v,0.80 mL total volume added) was added dropwise over 5 min to asuspension of zinc (1.622 g, 24.8 mmol) in DMA (12 mL) underargon atmosphere. The mixture was stirred for 15 min before benzyl4-iodopiperidine-1-carboxylate19 (7.13 g, 20.7 mmol) wasadded dropwise over 15 min as a solution in DMA (6 mL). This mixturewas stirred for an additional 15 min before adding to quinoxaline71 below.The above (1-((benzyloxy)carbonyl)piperidin-4-yl)zinc(II)iodide (8.49 g, 20.7 mmol) solution was added slowly to a suspensionof 2-chloro-3-((1-(quinolin-2-yl)azetidin-3-yl)oxy)quinoxaline71 (5.0 g, 13.8 mmol), copper(I) iodide (0.262 g,1.378 mmol), and Pd(dppf)Cl2 dichloromethane adduct (0.56 g,0.69 mmol) in DMA (15 mL) under argon. This mixture was stirredat 80 C for 2 h, then cooled to room temperature. EtOAcwas added and the suspension was filtered through Celite toremove insoluble material. The filtrate was then diluted withmore EtOAc and then washed with water (3), brine (1), dried(MgSO4), filtered, and concentrated in vacuo to give an oil. Thisoil was purified by silica gel chromatography eluting with0-100% EtOAc/hexane to give 6.93 g (92%) of the title compoundan off-white solid.

As the paragraph descriping shows that 885275-00-3 is playing an increasingly important role.

Reference：
Article; Rzasa, Robert M.; Frohn, Michael J.; Andrews, Kristin L.; Chmait, Samer; Chen, Ning; Clarine, Jeffrey G.; Davis, Carl; Eastwood, Heather A.; Horne, Daniel B.; Hu, Essa; Jones, Adrie D.; Kaller, Matthew R.; Kunz, Roxanne K.; Miller, Silke; Monenschein, Holger; Nguyen, Thomas; Pickrell, Alexander J.; Porter, Amy; Reichelt, Andreas; Zhao, Xiaoning; Treanor, James J.S.; Allen, Jennifer R.; Bioorganic and Medicinal Chemistry; vol. 22; 23; (2014); p. 6570 – 6585;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

50607-30-2, Piperidine-2,4-dione is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 13 2-PYRIMIDIN-4-YT-1, 5, 6, 7-TETRAHYDRO-4H-PYRROLO JL 3, 2-CIPVRIDIN-4-O. NE HYD ROCHLORIDE 2-BROMO-1-PYRIMIDIN-4-YLETHANONE hydrobromide (67 mg, 0.239 MMOLS), piperidine-2,4-dione (50 mg, 0.358 MMOLS) and ammonium acetate (74 mg, 0.957 MMOLS) were dissolved in anhydrous ethanol (1 mL) and stirred at r. t. overnight. The reaction mixture was concentrated to dryness under reduced pressure and the residue was taken up with water (1 mL) and filtered; the solid was washed with cold water and dried. To the obtained brown solid (30 mg) dissolved in MEOH (15 mL), 4N HCI in dioxane (0.5 mL) was added and the mixture was stirred for 30 minutes and then concentrated under reduced pressure to half of the volume. The obtained precipitate was filtered, washed with ethyl acetate and dried to give the title compound as a yellow solid (31 mg, Y=52percent).

50607-30-2, As the paragraph descriping shows that 50607-30-2 is playing an increasingly important role.

Reference：
Patent; PHARMACIA & ITALIA S.p.A.; WO2005/14572; (2005); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem