Heterocyclic Building Blocks-piperidine

191732-76-0, 5-Amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 5-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione (2) (30 mg, 0.11 mmol) in DMF (1 mL) was added Cs2CO3 (35.77 mg, 0.11 mmol) and CH3I (0.01 ml, 0.11 mmol) at room temperature. The reaction mixture was stirred for 2 h at the same temperature, and additional 1 eq of CH3I (0.01 ml, 0.11 mmol) was added. Reaction mixture stirred for an additional 2 h at room temperature. The reaction was diluted with AcOEt (10 mL) and then quenched with aqueous HCl (1 N, 1 mL), the pH was adjusted to 7-8 using an aqueous solution of NaHCO3. Organic phase was separated, washed with brine (5 mL, 5*), dried (Na2SO4), and evaporated under vacuum. Crude product was purified by PTLC (DCM:MeOH:NH4OH, 90:9:1) to give 28 mg of pure product (3) as a yellow solid (88% yield). 1H NMR (500 MHz, DMSO-d6) delta 7.52 (d, J=8.2 Hz, 1H), 6.94 (d, J=2.0 Hz, 1H), 6.83 (dd, J=8.2, 1.5 Hz, 2H), 6.57 (s, 2H), 5.09 (dd, J=13.0, 5.3 Hz, 1H), 3.00 (s, 3H), 2.96-2.85 (m, 1H), 2.78-2.68 (m, 1H), 2.61-2.43 (m, 1H), 2.01 (ddd, J=9.9, 5.5, 2.7 Hz, 1H). 13C NMR (151 MHz, DMSO-d6) delta 172.24, 170.35, 168.08, 167.56, 155.70, 134.63, 125.69, 117.38, 116.56, 107.49, 49.59, 31.57, 27.02, 21.85 LC/MS (ESI); m/z [M+H]+ Calcd. for C14H14N3O4, 288.0984. Found 288.0987., 191732-76-0

The synthetic route of 191732-76-0 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Yale University; Crews, Craig M.; Jaime-Figueroa, Saul; Toure, Momar; US2019/276459; (2019); 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

Into a 250-mL round-bottom flask, was placed tert-butyl 3-cyano-4-oxopiperidine-l-carboxylate (5 g, 22.30 mmol, 1.00 equiv), NH2NH2H20 (11.1 g, 223 mmol, 10.00 equiv), EtOH (100 mL). The resulting solution was stirred overnight at 25 oC. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with chloroform/methanol (95/5). This resulted in 4.9 g (93%) of tert-butyl 3-amino-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridin-5-carboxylate as a white solid. MS (ES, m/z) [M+H]: 239.

914988-10-6 tert-Butyl 3-cyano-4-oxopiperidine-1-carboxylate 42609283, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; THE ROCKEFELLER UNIVERSITY; PONDA, Manish P.; SELNICK, Harold; EGBERTSON, Melissa; BRESLOW, Jan L.; (179 pag.)WO2019/108565; (2019); 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.3518-83-0,N-Ethyl-4-hydroxypiperidine,as a common compound, the synthetic route is as follows.

Add to the reaction flask1-ethylpiperidin-4-ol (1.0 g, 7.7 mmol), 2,5-dibromopyridine (2 g, 8.5 mmol)And dimethylsulfoxide (30 mL) were added sodium tert-butoxide (1.7 g, 15.4 mmol).The mixture was stirred at room temperature for 3 hours, water (30 mL) was added,Dichloromethane extraction (20 mL x 3) .The organic layers were combined,Washed with saturated brine (20 mL), dried over anhydrous sodium sulfate and the filtrate was concentrated in vacuo.The resulting residue was purified by column chromatography (DCM / MeOH = 10: 1)To give the title compound (702 mg, black solid) in 32% yield., 3518-83-0

As the paragraph descriping shows that 3518-83-0 is playing an increasingly important role.

Reference：
Patent; Gan & Lee Pharmaceuticals; Liu, Wenjian; Yin, Lei; Li, Heng; (94 pag.)CN106608879; (2017); 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.5810-56-0,4-Acetamidopiperidine,as a common compound, the synthetic route is as follows.

20.1 c lambda/-(1-{4-[2-(4-Benzyloxy-6-oxo-6/-/-pyrimidin-1-yl)-ethyl]-benzyl}-piperidin-4-yl)- acetamideTo 100 mg (0.25 mmol) 6-benzyloxy-3-[2-(4-bromomethyl-phenyl)-ethyl]-3H-pyrimidin-4-one (example 20.1 b) in 1.0 mL DCM is added 71 mg (0.50 mmol) lambda/-piperidin-4-yl-acetamide atRT. The reaction mixture is refluxed for 2 h and the solvent is evaporated. The residue is dissolved in DMF and a few drops of formic acid and is transferred to a reverse HPLC for purification (Waters symmetry, C 18; water (0.15 % formic acid)/acetonitrile 95:5 to 5:95).Yield: 75 mg (65% of theory) ESI Mass spectrum: [M+H]+ = 461Retention time HPLC: 2.2 min (method G).

5810-56-0, 5810-56-0 4-Acetamidopiperidine 1445156, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2008/22979; (2008); 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.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’-tetramethylethylenediamine (0.335 g, 2.89 mmol) in TEtaF (1 mL) was added n-butyllithium (2.5M, 1.15 rnL, 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 TEDF (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 TEtaF (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 NaEtaCOs 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: m/z = 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.; WO2007/16087; (2007); 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.72551-53-2,Ethyl 1-benzylpiperidine-3-carboxylate,as a common compound, the synthetic route is as follows.

72551-53-2, General procedure: To a stirred solution of the carboxylate (1.50 g, 7.85 mmol, 1.0eq.) in toluene (25 ml), was added Red-Al (65 wt % in toluene,3.66 g, 3.54 ml, 11.8 mmol, 1.5 eq.) at 15-20 C. The contents were stirred overnight at rt. The reaction was quenched by the slowaddition of 10% sodium hydroxide (~1 ml) and then the addition ofwater. The contents were stirred for 30 min, and the toluene layerwas separated, washed with a saturated solution of sodium chloride.The organic layer was dried (anhydrous sodium sulfate), filtered and evaporated in vacuo to yield the alcohol which was used without any further purification

72551-53-2 Ethyl 1-benzylpiperidine-3-carboxylate 2736370, apiperidines compound, is more and more widely used in various fields.

Reference：
Article; van Greunen, Divan G.; Cordier, Werner; Nell, Margo; van der Westhuyzen, Chris; Steenkamp, Vanessa; Panayides, Jenny-Lee; Riley, Darren L.; European Journal of Medicinal Chemistry; vol. 127; (2017); p. 671 – 690;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

72752-52-4, 2-Piperidinobenzonitrile is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 3-5; 4-methyl-2-(2-(1-piperidinyl)phenyl)pentanoic acid; This acid was synthesized in 3 steps from the intermediate 2-(1-piperidinyl)benzonitrile (see example 2-1). Step 1; 3-methyl-1-(2-(1-piperidinyl)phenyl)butan-1-ol; Under anhydrous atmosphere, 2-(1-piperidinyl)benzonitrile (10 g, 53.7 mmol) was solubilized in anhydrous THF (50 ml). Freshly prepared isobutylmagnesium bromide (83 ml at 3.9 mol/l in THF, 324 mmol) was added and the mixture was refluxed overnight. The mixture was hydrolyzed with water and acidified by a 1M HCl solution until pH 7. The resulting ketone was extracted by ethyl acetate, dried with magnesium sulfate (MgSO4), and evaporated. The residue was solubilized in methanol (100 ml) and the solution was cooled with an ice bath. Sodium borohydride (7.1 g, 188 mmol) was added portionwise at 0 C. and the reaction was slowly warmed to room temperature. Once the ketone was reduced, water was added and the alcohol was extracted by ethyl acetate, dried with magnesium sulfate (MgSO4) and evaporated. The expected product was purified by silica gel chromatography (cyclohexane/ethyl acetate 95/5). Yield: 60%, 72752-52-4

72752-52-4 2-Piperidinobenzonitrile 2774355, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; GENFIT; US2006/79696; (2006); 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.19099-93-5,1-Cbz-Piperidin-4-one,as a common compound, the synthetic route is as follows.

Step B. Benzyl T-chloro^’-oxo-l’^’-dihvdro-lH-spirorpiperidine^^’-pyridopj-difUloxazine]-.- carboxylate; To a -20 0C solution of N,N,N’,N’-tetramethylethylenediamine (0.335 g, 2.89 mmol) in TEtaF (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 fe/t-butyl (6-chloropyridin-2-yl)carbamate (0.300 g, 1.31 mmol) in TEtaF (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 TEtaF (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 NaEtaCU3 was added and the mixture extracted with EtOAc (3x). The combined organic layers were washed with H2O, brine, dried over MgSC>4, 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

As the paragraph descriping shows that 19099-93-5 is playing an increasingly important role.

Reference：
Patent; MERCK & CO., INC.; WO2006/41830; (2006); A2;,
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

[0313] Step a: To a stirred suspension of 1-(2-methoxy-6-methylphenyl)hydrazine hydrochloride (3.77 g, 20.0 mmol) in EtOH (50 mL) and glacial acetic acid (10 mL, 208 mmol) was added tert-butyl 3-cyano-4-oxopiperidine-1-carboxylate (4.5 g, 22.0 mmol) at room temperature. The resulting mixture was stirred under reflux for 16 h. After removal of solvent under reduced pressure, the residue was dissolved in EtOAc and washed with aqueous NaOH (2 N), brine, and dried over MgSO4. The solvent was removed under reduced pressure and the residue was purified by silica gel flash chromatography (5 to 55% EtOAc in hexanes) to give tert-butyl 3-amino-2-(2-methoxy-6-methylphenyl)-6,7-dihydro-2H-pyrazolo[4,3-c]pyridine- 5(4H)-carboxylate . MS: (ES) m/z calculated for C19H27N4O3 [M + H]+ 359.2, found 359.2. Caution: Diazonium formation could be potentially dangerous, please handle with care and ware proper personal protection equipment.

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

Reference：
Patent; CHEMOCENTRYX, INC.; FAN, Pingchen; LANGE, Christopher W.; LUI, Rebecca M.; MALATHONG, Viengkham; MALI, Venkat Reddy; PUNNA, Sreenivas; SINGH, Rajinder; TANAKA, Hiroko; ZENG, Yibin; ZHANG, Penglie; (284 pag.)WO2018/222598; (2018); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

936130-82-4, Methyl 4-(piperidin-4-yl)benzoate hydrochloride is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

936130-82-4, Synthesis of 4-[l-(4-formyl-phenyl)-piperidin-4-yl-|-benzoic acid methyl ester (1). A mixture of 4-(4-methoxycarboxyphenyl) piperidine HCl (256 mg, 1.0 mmol), 4-fluoro-benzaldehyde (105 mul, 1.0 mmol) and K2CO3 (250 mg, 1.8 mmol) in DMF (5 ml) was stirred at ambient temperature overnight. Reaction was diluted with water (30 ml). Formed precipitate was filtrated, washed with water (20 ml) and ether (20 ml), and dried in vacuum overnight to provide target compound (1) (203 mg, 63%) as white solid. LC-MS [M+H] 324.3 (C20H21NO3+H, requires 324.41).

936130-82-4 Methyl 4-(piperidin-4-yl)benzoate hydrochloride 42614593, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; ACHAOGEN, INC.; WO2008/154642; (2008); A2;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem