Heterocyclic Building Blocks-piperidine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.38385-95-4,2-(Piperidin-4-yl)-1H-benzo[d]imidazole,as a common compound, the synthetic route is as follows.,38385-95-4

In a round bottomed flask equipped with a magnetic stir bar and a nitrogen inlet, a mixture of vanillic acid (501 mg, 2.98 mmol), EDC hydrochloride (571 g, 2.98 mmol) and HOBt-hydrate (456 mg, 2.98 mmol) and DIPEA (0.86 mL, 8.97 mmol) in 18 mL DMF were added. The mixture was then stirred at room temperature for one hour. To the above solution, 2- (piperidin-4-yl)-lH-benzo[d]imidazole (600 mg, 2.98 mmol) was added. The mixture was stirred at room temperature for ovemight. To the reaction mixture water was added, precipitate was filtered and dried in vacuo yielding 724 mg of (4-(lH-benzo[cf]imidazol-2-yl)piperidin-l- yl)(4-hydroxy-3-methoxyphenyl)methanone as crude product. To the crude product, CH2CI2 was added, white precipitate formed was filtered and then dried in vacuo to give 334 mg (32 %) of the desired product. (0349) XH NMR (400 MHz, DMSO-d6) delta 12.19 (s, 1H), 9.40 (s, 1H), 7.50 (d, J= 8.0 Hz, 1H), 7.38 (d, J= 7.6 Hz, 1H), 7.19 – 7.02 (m, 2H), 6.93 (s, 1H), 6.89 – 6.64 (m, 2H), 3.75 (s, 3H+1H masked), 3.20 – 2.94 (m, 4H), 2.10 – 1.88 (m, 2H), 1.75 (q, J= 13.5, 13.0 Hz, 2H).

38385-95-4 2-(Piperidin-4-yl)-1H-benzo[d]imidazole 715810, apiperidines compound, is more and more widely used in various fields.

Reference£º
Patent; ARIZONA BOARD OF REGENTS ON BEHALF OF THE UNIVERSITY OF ARIZONA; KHANNA, May; KHANNA, Rajesh; GOKHALE, Vijay; CHAWLA, Reena; (186 pag.)WO2018/144900; (2018); A1;,
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3970-68-1, 4-Methylpiperidin-4-ol is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[0593] N-( 4-chloro-5-cyanopyridin-2-yl)-7-( dimethoxymethyl)-3,4-dihydro-1 ,8-naphthyridine-1 (2H)carboxamide(intermediate 21, 50 mg, 0.129 mmol) and4-methylpiperidin-4-ol (21.5 mg, 0.142 mmol) were dissolvedin DMF (1 ml) under argon. The mixture was stirred at100 C. for 16 h.[0594] An excess of 4-methylpiperidin-4-ol was added tothe mixture and stirred for 45 min at 100 C. The reactionmixture was diluted in EtOAc and washed 2x with sat. aq.NH4 Cl and brine. The organic layer was dried over Na2S04 ,filtered and concentrated under vacuum. The crude materialwas purified by normal phase chromatography ( 4 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100) to give the titlecompound as an off-white solid. (UPLC-MS 3) tR 1.08 min;ESI-MS 467.2 [M+Ht., 3970-68-1

The synthetic route of 3970-68-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Novartis AG; Buschmann, Nicole; Fairhurst, Robin Alec; Furet, Pascal; Knoepfel, Thomas; Leblanc, Catherine; Liao, Lv; Mah, Robert; Nimsgern, Pierre; Ripoche, Sebastien; Xiong, Jing; Han, Bo; Wang, Can; Zhao, Xianglin; US2015/119385; (2015); A1;,
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73579-08-5,73579-08-5, 1-Methyl-4-(methylamino)piperidine is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4-(5-Cyclohexylimino-4-methyl-4,5-dihydro-[1,3,4]thiadiazol-2-yl)-N-methyl-N-(1-methyl-piperidin-4-yl)-benzamide To a solution of I37.1 (0.5 mmol, 200 mg) in DMF (2.5 mL), ethyl-diisopropyl-amine (1.6 mmol, 190 muL), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.6 mmol, 265 mg), 1-hydroxy-7-azabenzotriazole (0.25 mmol, 34 mg) and 1-methyl-4-(methylamino)piperidine (0.6 mmol, 87 muL) were added, and the reaction mixture was stirred at RT overnight. The solvent was distilled under reduced pressure, and the residue was poured into water before extraction with dichloromethane. The organic layer was washed with brine and then with a saturated solution of NaHCO3, dried over magnesium sulfate, filtered, and concentrated under vacuum. The residue was purified by silica gel chromatography using a gradient of dichloromethane containing 0percent to 15percent methanol, to give the desired product. Yield: 93.5percent. 1H-NMR (400 MHz, DMSO) delta ppm: 1.23-1.45 (m, 5H), 1.55-1.65 (m, 1H), 1.68-1.85 (m, 6H), 1.85-2.00 (m, 2H), 2.23-2.44 (m, 5H), 2.55-2.65 (m, 1H), 2.83 (s, 3H), 3.00-3.10 (m, 2H), 3.55 (s, 3H), 3.85-4.03 (m, 1H), 7.48 (dd, 2H), 7.70 (dd, 2H). MS (m/z)/M+1=428.

As the paragraph descriping shows that 73579-08-5 is playing an increasingly important role.

Reference£º
Patent; Vergne, Fabrice; Ducrot, Pierre; Andrianjara, Charles; Bernardelli, Patrick; Lorthois, Edwige; US2003/45557; (2003); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.159635-49-1,tert-Butyl 4-methylenepiperidine-1-carboxylate,as a common compound, the synthetic route is as follows.

To a solution of tert-butyl 4-methylenepiperidine-1-carboxylate (APOLLO, 10 g, 50. 7 mmol) in dioxane (130 mL) at 0 ¡ãC, a solution of HCI 4M in dioxane (ALFA-AESAR, 130mL, 507 mmol, 10 eq) was added and the mixture was stirred at rt overnight. Monitoring by UPLC and TLC showed the reaction was completed. The solvent was removed under vacuum to afford the desired compound 4-methylidenepiperidine hydrochloride which was used in the next step without further purification (7.6 g, 100percent).1H NMR (400MHz, DMSO-cfe) delta ppm: 9.19 (br s, 2H), 4.86 (s, 2H), 3.06 (t, J = 6.0 Hz, 4H), 2.41 (t, J = 6.0 Hz, 4H)., 159635-49-1

As the paragraph descriping shows that 159635-49-1 is playing an increasingly important role.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BIOVERSYS AG; PORRAS DE FRANCISCO, Esther; REMUINAN-BLANCO, Modesto Jesus; BOUROTTE, Marilyne; DEPREZ, Benoit; WILLAND, Nicolas; (43 pag.)WO2019/34700; (2019); A1;,
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216854-23-8, (S)-tert-Butyl piperidin-3-ylcarbamate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 60[0375] Synthesis of l-((S)-3-(2-aminopyrirmdin-4-ylamino) piperidin-l-yl)-2-(3,5- dichlorophenylamino)ethanone:Reagents and conditions: a) 2-(3,5-dichlorophenylamino)acetic acid, EDCI, HOBt, DIEA, DMF, rt, 15 h; b) 4 N HCl in 1,4-dioxane, rt, 1 h; c) 4-chloropyrimidin-2- amine, DIEA, n-BuOH, 100 C, 2 days.[0376] Synthesis of ieri-butyl (lS’)-l-(2-(3,5-dichlorophenylamino)acetyl)piperidin-3- ylcarbamate: To a solution of ieri-butyl (^-piperidin-S-ylcarbamate (500 mg, 2.5 mmol), in DMF (5 mL) was added EDCI (573 mg, 3.0 mmol), HOBt (405 mg, 3.0 mmol), 2-(3,5- dichlorophenylamino)acetic acid (550 mg, 2.5 mmol) and DIEA (0.5 mL, 3.0 mmol) at 0 C. The reaction mixture was stirred at rt overnight, the reaction mixture was diluted with EtOAc and washed with water. The water layer was extracted with the EtOAc and the combined organic layer was dried over Na2S04 and evaporated in vacuo to give the crude compound that was purified by column chromatography (silica gel, gradient MeOH in CH2CI2) to afford (900 n 98%) of the titled intermediate. LCMS: m/z: [M+l] = 402., 216854-23-8

216854-23-8 (S)-tert-Butyl piperidin-3-ylcarbamate 1514171, apiperidines compound, is more and more widely used in various fields.

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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343788-69-2, 1-Boc-4-Amino-4-methylpiperidine is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 284; tert-Butyl 4-[7-faminocarbonyl)-2H-indazol-2-yll-4-methylpiperidine-l-carboxylate (TJU3); Step 1: tert-Butyl 4-{[3-(methoxycarbonyl)-2-nitrobenzylidene]amino}-4-methylpiperidine- 1-carboxylate (UUl).; A mixture of methyl 3-formyl-2-nitrobenzoate Example 1, (A3) (1.0 eq.) and tert-butyl 4-amino- 4-methylpiperidine- 1-carboxylate (WO 2005/101989)(1.05 eq.) in EtOH (0.2 M) was stirred at reflux for 24 hr. Evaporation of the solvent gave the title imine which was used in the next step without further purification., 343788-69-2

The synthetic route of 343788-69-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI SPA; WO2007/113596; (2007); A1;,
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84163-13-3, 6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,84163-13-3

A mixture of 6-fluoro-3- (4-piperidinyl) -1,2-benzisoxazole hydrochloride was added to 400 mL of DMF, and potassium carbonate35 g, 3.5 g of potassium iodide and 33.5 g of 3-methoxy-4- (3-chloropropoxy) acetophenone were added and heated for about 7 h. Cold to room temperature, pumpingFilter, the filtrate stirring into the 1000mL cold water, stirring about 2h, pumping, washing, drying, light yellow crude 53g. EthanolAfter recrystallization, 28 g of iloperidone was obtained and the content of ILPI-07 was 0.12%.

The synthetic route of 84163-13-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Beijing Pharmaceutical Group Co., Ltd.; Wang Qichang; Liu Moyi; Liu Qingliang; Zou Jiang; Yang Yan; (9 pag.)CN106831742; (2017); A;,
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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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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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149353-75-3, 4-(1-(tert-Butoxycarbonyl)piperidin-4-yl)benzoic acid is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Production Example 1-8 tert-Butyl 4-(4-((4-((6-methoxy-1-(methylcarbamoyl)-1H-indol-5-yl)oxy)pyridin-2-yl)carbamoyl)phenyl)piperidine-1-carboxylate Benzotriazole (2.32 g, 19.5 mmol) was dissolved in dichloromethane (100 mL), thionyl chloride (1.4 mL, 19.2 mmol) was added under nitrogen atmosphere at room temperature, and the mixture was stirred for 5 minutes. 4-(1-(tert-Butoxycarbonyl)piperidin-4-yl)benzoic acid described in Production Example 1-12 (5.4 g, 17.7 mmol) was added to the reaction mixture at mom temperature, and the mixture was stirred for 25 minutes. The reaction mixture was filtered through a glass filter entirely covered with anhydrous sodium sulfate and then washed with dichloromethane, then the filtrate was added to a mixture of 5-((2-aminopyridin-4-yl)oxy)-6-methoxy-N-methyl-1H-indole-1-carboxamide described in Production Example 1-6 (2.5 g, 8.01 mmol), triethylamine (11 mL, 79.4 mmol), and 4-dimethylaminopyridine (101 mg, 0.827 mmol) in tetrahydrofuran (80 mL) at 0 C. The resultant was stirred at mom temperature for 5 hours and then the reaction mixture was concentrated under vacuum. Water and ethyl acetate were added to the residue for partition, and the organic layer was washed with a saturated saline solution, and then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under vacuum, the residue was dissolved in tetrahydrofuran, an excessive quantity of 9.8 M methylamine methanol solution was added at room temperature, and the mixture was stirred for 50 minutes. The reaction mixture was concentrated under vacuum, the residue was dissolved in dichloromethane, and the resultant was purified with NH silica gel column chromatography (n-heptane:ethyl acetate=1:1-1:3-0:1). The target fraction was concentrated under vacuum and the precipitate was collected by filteration and washed with diethyl ether and ethyl acetate to obtain the title compound (3.15 g, 66%). The filtrate was combined with the mixture fraction and the resultant was concentrated under vacuum and dissolved in dichloromethane, and the resultant was purified with NH silica gel column chromatography (n-heptane:ethyl acetate=1:1-1:3-0:1). The target fraction was concentrated under vacuum and the precipitate was collected by filteration and washed with diethyl ether and ethyl acetate to obtain the title compound (264 mg, 5.5%). 1H-NMR Spectrum (CDCl3) delta (ppm): 1.48 (9H, s), 1.55-1.69 (2H, m), 1.77-1.87 (2H, m), 2.64-2.89 (3H, m), 3.02-3.07 (3H, m), 3.86 (3H, s), 4.26 (2H, brs), 5.62 (1H, brs), 6.50-6.55 (1H, m), 6.61 (1H, dd, J=5.9, 2.2 Hz), 7.22 (1H, d, J=3.7 Hz), 7.27-7.33 (3H, m), 7.80 (2H, d, J=8.4 Hz), 7.90 (1H, d, J=2.2 Hz), 8.04 (1H, s), 8.09 (1H, d, J=5.9 Hz), 8.54 (1H, brs)., 149353-75-3

As the paragraph descriping shows that 149353-75-3 is playing an increasingly important role.

Reference£º
Patent; Eisai R&D Management Co., Ltd.; Funasaka, Setsuo; Okada, Toshimi; Tanaka, Keigo; Nagao, Satoshi; Ohashi, Isao; Yamane, Yoshinobu; Nakatani, Yusuke; Karoji, Yuki; US2014/235614; (2014); A1;,
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