Category: 20691-89-8

20691-89-8, 1-Methyl-4-piperidinemethanol is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 4-[(2, 4-dichloro-5-methoxyphenyl) amino3-6-ethoxy-7-fluoro-3- quinolinecarbonitrile (200 mg, 0.49 mmol), 1-methylpiperidine-4-methanol (1888 mg, 0.98 mmol) (WO 20047212) and sodium hydride (196 mg, 4.6 mmol) in 5 mL of N, N-dimethylformamide was heated at 125C for 3 hours. The reaction mixture was poured into saturated sodium bicarbonate and stirred for 1 hour. The solid was collected by filtration, washed with water and dried in vacuo. The solid was purified by preparative thin layer chromatography, eluting with 15% methanol in dichloromethane. Trituation with diethyl ether provided 67 mg of 4-[(2,4-dichloro-5- methoxyphenyl) amino]-6-ethoxy-7- [ (1-methylpiperidin-4-yl) methoxy] quinoline-3- carbonitrile as a light brown solid, mp 182-186C. MS 513. 0 (M-H)- Analysis for C2gH28CI2N403-1. 4 H20 Calcd : C, 57.76 ; H, 5.74 ; N, 10.36. Found: C, 57.65 ; H, 5.43 ; N, 10.15., 20691-89-8

As the paragraph descriping shows that 20691-89-8 is playing an increasingly important role.

Reference：
Patent; WYETH; WO2005/47259; (2005); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

20691-89-8, 1-Methyl-4-piperidinemethanol is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of l-chloro-4-nitrobenzene (23) (2.37 g, 15.0 mmol), alcohol 22 (1.94 g, 15.0 mmol), and DMSO (25 mL) was treated portionwise with NaH (60% in mineral oil, 660 mg, 16.5 mmol) at 40 0C. The mixture was stirred at 70 0C for 3 h, poured into water (15O mL), and extracted with Et2O (5 x 10O mL). The combined organic fractions were washed with water (250 mL) and brine (250 mL), dried (MgSQ4), and the solvent was removed in vacuo. The resulting solid was recrystallized from Et2O to give 24 (3.12 g, 83%) as yellow needles. 1H NMR (300 MHz, CDCl3): delta = 1.36-1.56 (m, 2 H, 3-Hax, 5-Hax), 1.75-1.91 (m, 3 H, 3-Heq, 4-H, 5-Heq), 1.98 (dt, J= 11.9, 1.9 Hz, 2 H, 2-Hax, 6-Hax), 2.30 (s, 3 H, NMe), 2.85-2.98 (m, 2 H, 2-Heq, 6-Heq), 3.90 (d, J= 5.8 Hz, 2 H, OCH2), 6.94 (me, 2 H, 2′-H, 6′-H), 8.19 Cm0, 2 H, 3′-H, 5′-H) ppm. – 13C NMR (50.3 MHz, CDCl3): 6 = 28.9 (C-3, C-5), 35.1 (C-4), 46.4 (NMe), 55.3 (C-2, C-6), 73.3 (OCH2), 114.3 (C-21, C-6′), 125.8 (C-3′, C-5′), 141.3 (C-41), 164.1 (C-I’) ppm. -MS (70 eV, EI): m/z (%) = 250 (79) [M]+, 249 (100) [M-H]+. – Ci3H]8N2O3 (250.29): calcd. C 62.38, H 7.25; found C 62.25, H 7.40., 20691-89-8

The synthetic route of 20691-89-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; SYNTARGA B.V.; GEORG-AUGUST-UNIVERSITAet GOeTTINGEN STIFTUNG OeFFENTLICHEN RECHTS (OHNE BEREICH HUMANMEDIZIN); WO2007/89149; (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.20691-89-8,1-Methyl-4-piperidinemethanol,as a common compound, the synthetic route is as follows.,20691-89-8

(1-Methyl-piperidin-4-yl)-methanol (2. 5USD g, 20 mmol) and hydroxy-diphenyl-acetic acid methyl ester (9. 69 g, 40 mmol) are suspended in toluene (65 ml). Molecular sieve 4A (1 g) is added and the mixture is stirred at room temperature for 10 minutes. Sodium (0.08 g) is added and the reaction mixture stirred at 80OC for 3 hours. Additional sodium (0.1 g) is then added and heating maintained at 80OC for 18 hours. The reaction mixture is cooled to room temperature, solid filtered off, and washed with ethylacetate. The filtrate is washed once with saturated aqueous NAHCO3 solution (50 ml) and twice with aqueous HCL 1M (25 ml each). The combined acidic aqueous layers are basified with saturated aqueous NAHCO3 solution and solid NAHCO3, the resulting precipitate is removed by filtration, drying under vacuum gives the title product as a white solid (M+H) + : 340.09.

20691-89-8 1-Methyl-4-piperidinemethanol 271971, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/815; (2005); 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.20691-89-8,1-Methyl-4-piperidinemethanol,as a common compound, the synthetic route is as follows.

Example 3b An alternative method of preparation is as follows: Triphenylphosphine (615mg, 2.3mmol) followed by diethyl azodicarboxylate (369mul, 2.3mmol) were added to a solution of 4-hydroxymethyl-1-methylpiperidine (151mg, 1.1mmol), (J Med. Chem 1973, 16, 156), and 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (250mg, 0.78mmol), (prepared as described for the starting material in Example 7), in methylene chloride (5ml). After stirring for 30 minutes at ambient temperature, 4-hydroxymethyl-1-methylpiperidine (51mg, 0.39mmol), triphenylphosphine (102mg, 0.39mmol) and diethyl azodicarboxylate (61mul, 0.39mmol) were added. After stirring for 15 minutes, the volatiles were removed under vacuum and the residue was purified by column chromatography eluding with methylene chloride/acetonitrile/methanol (70/10/20 followed by 75/5/20 and 80/0/20). The fractions containing the expected product were combined and the volatiles were removed by evaporation. The residue was dissolved in a mixture of methylene chloride and methanol and 5M hydrogen chloride in isopropanol was added. The suspension was concentrated and the solid was collected by filtration, washed with ether and dried under vacuum to give 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline hydrochloride (16mg, 4%)., 20691-89-8

As the paragraph descriping shows that 20691-89-8 is playing an increasingly important role.

Reference：
Patent; AstraZeneca AB; EP1244647; (2006); 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.20691-89-8,1-Methyl-4-piperidinemethanol,as a common compound, the synthetic route is as follows.

Example 24 1-Methyl-4-(4-nitrophenoxymethyl)piperidine (24): A mixture of 1-chloro-4-nitrobenzene (23) (2.37 g, 15.0 mmol), alcohol 22 (1.94 g, 15.0 mmol), and DMSO (25 mL) was treated portionwise with NaH (60% in mineral oil, 660 mg, 16.5 mmol) at 40 C. The mixture was stirred at 70 C. for 3 h, poured into water (150 mL), and extracted with Et2O (5*100 mL). The combined organic fractions were washed with water (250 mL) and brine (250 mL), dried (MgSO4), and the solvent was removed in vacuo. The resulting solid was recrystallized from Et2O to give 24 (3.12 g, 83%) as yellow needles. 1H NMR (300 MHz, CDCl3): delta=1.36-1.56 (m, 2H, 3-Hax, 5-Hax), 1.75-1.91 (m, 3H, 3-Heq, 4-H, 5-Heq), 1.98 (dt, J=11.9, 1.9 Hz, 2H, 2-Hax, 6-Hax), 2.30 (s, 3H, NMe), 2.85-2.98 (m, 2H, 2-Heq, 6-Heq), 3.90 (d, J=5.8 Hz, 2H, OCH2), 6.94 (mc, 2H, 2′-H, 6′-H), 8.19 (mc, 2H, 3′-H, 5′-H) ppm. -13C NMR (50.3 MHz, CDCl3): delta=28.9 (C-3, C-5), 35.1 (C-4), 46.4 (NMe), 55.3 (C-2, C-6), 73.3 (OCH2), 114.3 (C-2′, C-6′), 125.8 (C-3′, C-5′), 141.3 (C-4′), 164.1 (C-1′) ppm. -MS (70 eV, EI): m/z (%)=250 (79) [M]+, 249 (100) [M-H]+. -C13H18N2O3 (250.29): calcd. C, 62.38; H, 7.25; found C, 62.25; H, 7.40., 20691-89-8

As the paragraph descriping shows that 20691-89-8 is playing an increasingly important role.

Reference：
Patent; Beusker, Patrick Henry; De Groot, Franciscus Marinus Hendrikus; Tietze, Lutz F.; Major, Felix; Joosten, Johannes Albertus Frederikus; Spijker, Henri Johannes; US2009/318668; (2009); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

20691-89-8, 1-Methyl-4-piperidinemethanol is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 57 ; 3-methoxv-4-I(I -methvlDiDeridin-4-Vl)methoxvlbenzonitrile; 53.3 ml of 1 N sodium bis (trimethylsilyl)amide added to a stirred solution of 6.63 g (51.3 mmol) of (1-methyl-piperidin-4-yl)-methanol in 14 ml of THF. After 20 minutes, solid 4-fluoro-3-methoxy benzonitrile was added. The mixture was refluxed for 20 minutes, cooled to room temperature and poured into water. The mixture was extracted with ethyl acetate. The organic extracts were dried over magnesium sulfate. The solvent was removed and the residue was recrystallized from ethyl acetate-hexanes yielding 8.9 g of the title compound as a white solid: mass spectrum (electrospray, m/e): M+H 261.2.

20691-89-8, 20691-89-8 1-Methyl-4-piperidinemethanol 271971, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; WYETH; WO2005/115145; (2005); 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.20691-89-8,1-Methyl-4-piperidinemethanol,as a common compound, the synthetic route is as follows.

To the solution of 3.04 g (14.51 mMol ; 1.25 Eq. ) of 3-N-BOC-Aminophenol and 3.81 g (14.51 [MMOL] ; 1.25 Eq. ) of triphenylphosphin (Aldrich T8, 440-9) under Argon in 30 mL of THF at [10C] is added dropwise a solution of 2.26 mL (14.51 mMol) of diethyl-azodicarboxylate (95%; Fluka 11624) in 6 mL of THF abs. After stirring for 10 min under ice cooling, a solution of 1.5 g (11.61 mMol ; 1 Eq. ) of 1-methyl-4-piperidinemethanol (Chem Pacific; 33077*) in 6 mL of THF abs. is added and kept for 20 min at [10C.] After 15 h at rt, the solvent is removed under reduced pressure and the reaction mixture is purified by column chromatography over silica gel [[SI60] (0,040-0, 063mm) Merck], eluting with [METHYLENCHLORID/METHANOL/NH3] (25% aqua) 70: 10: 0.8 to obtain [[3- (L-METHYL-PIPERIDIN-4-YLMETHOXY)-PHENYL]-CARBAMIC] acid tert-butyl ester. Title compound: ES-MS: 321.1 [M+H] [+] ; single peak at tR= 4.63 min (System 1). * [1-METHYL-4-PIPERIDINEMETHANOL] can alternatively be prepared from [PIPERIDIN-4-YL-METHANOL] and formaldehyde (36% in water) under reductive conditions [(H2/RANI] in CH30H) at rt., 20691-89-8

As the paragraph descriping shows that 20691-89-8 is playing an increasingly important role.

Reference：
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/5282; (2004); 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.20691-89-8,1-Methyl-4-piperidinemethanol,as a common compound, the synthetic route is as follows.

To a mixture of />-chloro nitrobenzene (6.0 g, 38 mmol) and l-methyl-4-piperidinemethanol (4.91 g, 38 mmol) in anhydrous DMSO (60 mL) was added NaH (1.82 g, 45.6 mmol) in small portions at room temperature under N2-atmosphere. After the addition was complete the reaction mixture was warmed at 40 0C and stirred for another 2h. The reaction was quenched with water, and the product was extracted with EtOAc. The organic layer was washed with brine and dried over Na2SO4. The crude product was recrystallized from ether to yield 6.6 g (69%) of the title compound as an orange solid. 1H NMR (400 MHz, CHLOROFORM-^) delta ppm 1.59 – 1.72 (m, 2 H) 1.92 (d, J=11.37 Hz, 3 H) 2.19 (t, J=I 1.49 Hz, 2 H) 2.44 (s, 3 H) 3.09 (d, J=I 1.12 Hz, 2 H) 3.93 (d, J=5.31 Hz, 2 H) 6.93 (d, J=9.2 Hz, 2 H) 8.20 (d, J=9.6 Hz, 2 H); [M+H] calc’d for Ci3H19N2O3, 251.2; found, 251.4., 20691-89-8

20691-89-8 1-Methyl-4-piperidinemethanol 271971, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2009/129401; (2009); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

20691-89-8, 1-Methyl-4-piperidinemethanol is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

20691-89-8, To a solution of OXO-THIOPHEN-2-YL-ACETYL chloride (31. 5 mmol) at 0 to 5OC in chloroform (60 ml) is added a solution of (1-METHYL-PIPERIDIN-4-YL)-METHANOL (4.07 g, 31.5 mmol) in chloroform (60 ml), dropwise maintaining the temperature below 5C. The resulting mixture is stirred for 2 hours at room temperature. Washing with 10% potassium carbonate solution, water and then drying over magnesium sulphate, filtration and evaporation gives the title compound.

The synthetic route of 20691-89-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/815; (2005); 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.20691-89-8,1-Methyl-4-piperidinemethanol,as a common compound, the synthetic route is as follows.

To Example 60 (0. 78 g, 6 mmol) was added thionyl chloride (10 mL) and the mixture was heated to reflux for about 2 hours. The mixture was cooled and concentrated to dryness. The residue was washed with acetone, suspended in saturated aqueous sodium carbonate and extracted with dichloromethane. The combined organic extracts were dried (Na2SO4), filtered and concentrated under vacuum to provide the desired product. MS (ESI) : m/z 148 (M+H) +.

20691-89-8, The synthetic route of 20691-89-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ABBOTT LABORATORIES; MAKOTO, Aoyama; WO2005/95387; (2005); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem