Category: 297172-16-8

297172-16-8, (4-Methylpiperidin-4-yl)methanol is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 4: 4-((4-methylpiperidin-4-yl)methoxy)-9-(2-trimethylsilanyl-ethoxymethyl)-9H- dipyridor2,3-b;4′,3′-dlpyrrole-6-carbonitrileTo a solution of (4-methylpiperidin-4-yl)methanol (989 mg, 7.7 mmol) in 1,4-dioxane (18 mL) and N,N-dimethylformamide (12 mL) was added sodium hydride as 60% dispersion in mineral oil (670 mg, 28 mmol). The reaction mixture was stirred at ambient temperature for 5 minutes before 4-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H- dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (428 mg, 1.2 mmol) was added in one portion and the reaction mixture was heated at 40C for 18 hours. The cooled reaction mixture was diluted with water (20 mL) and ethyl acetate (50 mL). The organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified flash chromatography (silica, 40 g, ISCO, 1-20% methanol in methylene chloride) to afford the title compound as an off-white solid, which was used in the next step without any further purification (300 mg, 56%).

297172-16-8, 297172-16-8 (4-Methylpiperidin-4-yl)methanol 22507737, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; F. HOFFMANN-LA ROCHE AG; DYKE, Hazel Joan; GAZZARD, Lewis J.; WILLIAMS, Karen; WO2011/73263; (2011); 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.297172-16-8,(4-Methylpiperidin-4-yl)methanol,as a common compound, the synthetic route is as follows.

4-methylpiperidin-4-yl)methanol (E4) (2.4 g, a mixture of the amino alcohol and NH4CO2H) was suspended in DCM (70 mL). Et3N (5 mL; 37.2 mmol) was then added followed by the drop-wise addition of ethyl chloroformate (1.05 mL, 13 mmol, 1.4 eq.). After 1 hr at room temperature, IN HCl (70 mL) was added and the layers were separated. The aqueous layer was extracted with DCM (70 mL) and the combined organic layers were dried over Na2SO4, filtered, and concentrated under high vacuum. The product obtained is an analytically pure oil (E5) and used without further purification. LC/MS m/z (M+l) 202.2, retention time 1.89 minutes; (10-99% CH3CN-H2O gradient with 0.03% TFA, 5 min). 1H NMR (400 MHz, DMSO-d6) delta 4.05 (q, J = 7.1 Hz5 2H), 3.66 {at, J= 13.6, 4.7 Hz, 2H), 3.32 (s, 2H), 3.11 (t, J = 5.2 Hz, IH), 3.11 (dd, J= 23.9, 3.5 Hz, IH), 1.44-1.37 (m, 3H), 1.26-1.22 (m, 2H), 1.19 (t, J = 7.1 Hz, 3H), 0.93 (s, 3H)., 297172-16-8

The synthetic route of 297172-16-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2007/100670; (2007); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

297172-16-8, (4-Methylpiperidin-4-yl)methanol is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(4-methylpiperidin-4-yl)methanol (E4) (2.4 g, a mixture of the amino alcohol and NH4CO2H) was suspended in DCM (70 mL). Et3N (5 mL; 37.2 mmol) was then added followed by the drop-wise addition of ethyl chloroformate (1.05 mL, 13 mmol, 1.4 eq.). After 1 h at room temperature, 1N HCl (70 mL) was added and the layers were separated. The aqueous layer was extracted with DCM (70 mL) and the combined organic layers were dried over Na2SO4, filtered, and concentrated under high vacuum. The product (E5) (1.7 g) is obtained analytically pure as an oil and used without further purification. LC/MS m/z (M+1) 202.2, tR 1.89 minutes; (10-99% CH3CN-H2O gradient with 0.03% TFA, 5 min). 1H NMR (400 MHz, DMSO-d6) delta 4.05 (q, J=7.1 Hz, 2H), 3.66 (dt, J=13.6, 4.7 Hz, 2H), 3.32 (s, 2H), 3.11 (t, J=5.2 Hz, 1H), 3.11 (dd, J=23.9, 3.5 Hz, 1H), 1.44-1.37 (m, 3H), 1.26-1.22 (m, 2H), 1.19 (t, J=7.1 Hz, 3H), 0.93 (s, 3H).

297172-16-8, As the paragraph descriping shows that 297172-16-8 is playing an increasingly important role.

Reference：
Patent; Makings, Lewis R.; Blanco, Miguel Garcia-Guzman; Hurley, Dennis J.; Drutu, Ioana; Raffai, Gabriel; Bergeron, Daniele M.; Nakatani, Akiko; Termin, Andreas P.; Silina, Alina; US2008/15179; (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.297172-16-8,(4-Methylpiperidin-4-yl)methanol,as a common compound, the synthetic route is as follows.

(4-methylpiperidin-4-yl)methanol (2.4 g, a mixture of the amino alcohol and NH4CO2H) was suspended in DCM (70 mL). Et3N (5 mL; 37.2 mmol) was then added followed by the drop-wise addition of ethyl chloroformate (1.05 mL, 13 mmol, 1.4 eq.). After 1 hour at room temperature, IN HCl (70 mL) was added and the layers were separated. The aqueous layer was extracted with DCM (70 mL) and the combined organic layers were EPO dried over Na2SCU, filtered, and concentrated under high vacuum. The product (1.7 g over 2 steps) is obtained analytically pure as an oil and used without further purification., 297172-16-8

297172-16-8 (4-Methylpiperidin-4-yl)methanol 22507737, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2006/58303; (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.297172-16-8,(4-Methylpiperidin-4-yl)methanol,as a common compound, the synthetic route is as follows.

69B. tert-Butyl 3-(4-((4-(hydroxymethyl)-4-methylpiperidin-1-yl)methyl)-3-methylphenoxy)azetidine-1-carboxylate To a solution of 69A (3.00 g, 10.3 mmol) in DCM (50 mL) was added (4-methylpiperidin-4-yl)methanol (2.56 g, 15.5 mmol) followed by DIPEA (3.60 mL, 20.6 mmol). The reaction mixture was stirred at RT for 20 min and then sodium triacetoxyborohydride (6.55 g, 30.9 mmol) was added. The mixture was stirred at RT overnight and then washed with a saturated aqueous solution of Na2CO3. The aqueous layer was extracted several times with DCM. The organic layers were filtered through a phase separator and then evaporated. There was obtained 3.1 g (74%) of the product as an oil. 1H NMR (500 MHz, CDCl3): delta 0.95 (s, 3H), 1.33 (m, 2H), 1.45 (s, 9H), 1.51 (m, 2H), 2.26 (m, 2H), 2.30 (s, 3H), 2.51 (m, 2H), 3.38 (s, 2H), 3.39 (s, 2H), 3.99 (m, 2H), 4.27 (m, 2H), 4.84 (m, 1H), 6.48 (dd, 1H), 6.56 (d, 1H), 7.16 (d, 1H), MS (APCI+) m/z 405 [M+H]+.

297172-16-8, As the paragraph descriping shows that 297172-16-8 is playing an increasingly important role.

Reference：
Patent; AstraZeneca AB; US2012/10189; (2012); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

297172-16-8, (4-Methylpiperidin-4-yl)methanol is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a mixture of TEA (6 mmol) and Boc20 (5 mmol) in DCM (40 mL) was added A14/15/16 (4.2 mmol), and stirred at rt overnight. The mixture was washed with IN HC1, NaHC03 and brine, dried over Na2S04, and concentrated in vacuo. The residue was purified through column chromatography to give the desired product.

297172-16-8, The synthetic route of 297172-16-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; NOVIRA THERAPEUTICS, INC.; HARTMAN, George D.; FLORES, Osvaldo A.; WO2013/96744; (2013); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

297172-16-8, (4-Methylpiperidin-4-yl)methanol is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 37 4-Hydroxymethyl-4-methyl-piperidine-1-carboxylic acid (7-[1,4]dioxepan-6-yl-4-methoxy-benzothiazol-2-yl)-amide Using 7-[1,4]dioxepan-6-yl-4-methoxy-benzothiazol-2-ylamine, phenyl chloroformate and 4-hydroxymethyl-4-methyl-piperidine, the title compound was prepared as light brown powder. MS: m/e=436(M+H+)., 297172-16-8

297172-16-8 (4-Methylpiperidin-4-yl)methanol 22507737, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Flohr, Alexander; Jakob-Roetne, Roland; Norcross, Roger David; Riemer, Claus; US2004/235915; (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.297172-16-8,(4-Methylpiperidin-4-yl)methanol,as a common compound, the synthetic route is as follows.

Example 76 (Preparation of Compound 77) A mixture of 4-fluoro-1-naphthonitrile (200 mg) (4-methyl-4-piperidinyl) methanol (242 mg), potassium carbonate (332 mg) and dimethylsulfoxide (3.0 mL) was stirred at 100C for 3 hours. After cooling to room temperature, the reactant was poured into water and extracted with ethyl acetate. The extracts were washed with water, dried and concentrated. The obtained residue was purified by silica gel column chromatography to obtain 4-[4-(hydroxymethyl)-4-methyl-1-piperidinyl]-1-naphthonitrile (256 mg) (Compound 77). mp 136 – 137C. 1H-NMR (300 MHz, CDCl3) delta: 1.10 (3H, s), 1.48 (1H, t, J=6.0 Hz), 1.55-1.61 (2H, m), 1.90 (2H, ddd, J=13.2, 10.2 and 4.2 Hz), 3.04-3.12 (2H, m), 3.24-3.31 (2H, m), 3.53 (2H, d, J=6.0 Hz), 7.04 (1H, d, J=8.1 Hz), 7.57 (1H, ddd, J=8.1, 6.9 and 1.5 Hz), 7.65 (1H, ddd, J=8.1, 6.9 and 1.5 Hz), 7.83 (1H, d, J=8.1 Hz), 8.15-8.21 (2H, m). IR (KBr) 2216, 1574 cm-1, 297172-16-8

As the paragraph descriping shows that 297172-16-8 is playing an increasingly important role.

Reference：
Patent; Takeda Pharmaceutical Company Limited; EP1553074; (2005); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

297172-16-8, (4-Methylpiperidin-4-yl)methanol is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Diisopropylamine (3.14 inL; 22.23 mmol; 1.1 eq.) was dissolved in THF (60 mL) and cooled to -78 C. Butyl lithium (2.5 M in hexane; 8.89 mL; 22.23 mmol; 1.1 eq.) was then added and the solution was stirred for 30 minutes at -78 C. Ethyl l-benzylpiperidine-4-carboxylate (5 g; 20.21 mmol; 1 eq.) was dissolved in THF (40 mL) and added to the LDA solution at -78 C. The solution was stirred at -78 C for 30 minutes and iodomethane (1.32 mL; 21.22 mmol; 1.05 eq.) was added. The solution was slowly warmed to room temperature and stirred at room temperature for 1 hour. Water (100 mL) was then added to the reaction followed by EtOAc (50 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2 x 50 mL). The combined organic layers were dried over Na2S04, filtered, and concentrated under reduced pressure to afford the product (5.0 g, 94% yield) as an oil. The product was analytically pure and used without further purification. LC/MS m/z (M+l) 262.0, Retention time 1.78 minutes; (10-99% CH3CN-H20 gradient with 0.03% TFA, 5 min). .H NMR (400 MHz, CDC13) 8 7.24-7.14 (m, 5H), 4.08 (q, J = 7.1 Hz, 2H), 3.40 (s, 2H), 2.60-2.57 (m, 2H), 2.08-2.02 (m, 4H), 1.47-1.40 (m, 2H), 1.17 (t, J = 7.1 Hz, 3H), 1.10 (s, 3H). [0210] l-Benzyl-4-methylpiperidine-4-carboxylate (5.0 g; 19.15 mmol) was dissolved in Et20 (50 mL) and cooled to 0 C. L1AIH4 (1.0 g; 26.3 mmol) was slowly added portion-wise to the solution. After the addition was complete, the solution was slowly warmed to room temperature and stirred for 1 h. The solution was then cooled to 0 C and slowly quenched with IN NaOH (6 mL). The resultant white precipitates were filtered and washed with EtOAc (100 mL). The combined organic layers were concentrated under reduced pressure to provide the product (3.9 g, 90% yield) as an oil which was used without further purification. LC/MS m/z M+l 220.0, retention time 0.64 minutes; (10-99% CH3CN-H20 gradient with 0.03% TFA, 5 min). .H NMR (400 MHz, CDCI3) 8 7.25-7.16 (m, 5H), 3.46 (s, 2H), 3.30 (d, J= 3.9 Hz, 2H), 2.51-2.46 (m, 2H), 2.26-2.20 (m, 2H), 1.52-1.45 (m, 3H), 1.30-1.25 (m, 2H), 0.87 (s, 3H). (l-benzyl-4-methylpiperidin-4-yl)methanol (3.9 g; 17.8 mmol) was dissolved in MeOH (50 mL) and NH4CO2H (12.5 g; 178.0 mmol) was added. Pd/C (10% by weight, wet; 5.5 g) was then added and the system was flushed with nitrogen and then with hydrogen. The reaction was stirred at room temperature overnight (18 h) and then filtered through a pad of Celite. The solvent was removed under high vacuum to provide a solid that was a mixture of the amino alcohol and NH4CO2H. The crude product (2.4 g as a mixture with NH4COOH) was used in the next step without further purification. LC/MS m/z (M+l) 130.0, retention time 0.35 min; (10-99% CH3CN-H2O gradient with 0.03% TFA, 5 min). .H NMR (400 MHz, CDCI3) 5 3.17 (s, 2H), 3.03-2.98 (m, 2H), 2.95-2.88 (m, 2H), 1.64-1.57 (m, 2H), 1.36-1.31 (m, 2H), 0.89 (s, 3H). [0212] (4-methylpiperidin-4-yl)methanol (2.4 g, a mixture of the amino alcohol andNELtCC^H) was suspended in DCM (70 mL). Et3N (5 mL; 37.2 mmol) was then added followed by the drop-wise addition of ethyl chloroformate (1.05 mL, 13 mmol, 1.4 eq.). After 1 hour at room temperature, IN HC1 (70 mL) was added and the layers were separated. The aqueous layer was extracted with DCM (70 mL) and the combined organic layers were dried over Na2S04, filtered, and concentrated under high vacuum. The product (1.7 g, 47% yield over 2 steps) is obtained analytically pure as an oil and used without further purification. LC/MS m/z (M+l) 202.2, retention time 1.89 minutes; (10-99% CH3CN-H2O gradient with 0.03% TFA, 5 min). .H NMR (400 MHz, DMSC-d6) 8 4.05 (q, J= 7.1 Hz, 2H), 3.66 (dt, J = 13.6,4.7 Hz, 2H), 3.32 (s, 2H), 3.11 (t, .7=5.2 Hz, 1H),3.11 (dd, .7=23.9, 3.5 Hz, 1H), 1.44-1.37 (m, 3H), 1.26-1.22 (m, 2H), 1.19 (t, J= 7.1 Hz, 3H), 0.93 (s, 3H).[0213] To a 100 mL round bottom flask was added DCM (30 mL) and oxalyl chloride (0.88 mL; 10.13 mmol). The solution was cooled to -78 C and treated with DMSO (1.19 mL; 16.88 mmol). The solution was stirred at -78 C for 20 minutes and then treated with ethyl 4-(hydroxymethyl)-4-methylpiperidine-l-carboxylate (1.7 g; 8.44 mmol, dissolved in 10 mL of DCM). The solution was stirred for 30 minutes at -78 C and then treated with Et3N (3.53 mL; 25.32 mmol). The solution was stirred at -78 C for 20 min and then slowly warmed to room temperature and stirred at room temperature for an additional 2 h. The solution was then treated with saturated aqueous NaHCC>3 (50 mL), diluted with DCM (50 mL), and the layers were separated. The organic layer was washed with brine (50 mL), dried over Na2SC>4, filtered, and concentrated under reduced pressure to afford 1.6 g (95% yield) of the product as an oil which was used without further purification. LC/MS m/z (M+l) 200.0, retention time 2.23 minutes; (10-99% CH3CN-H2O gradient with 0.03% TFA, 5 min). .H NMR (400 MHz, CDC13) 5 9.40 (s, 1H), 4.06 (q, J= 7.1 Hz, 2H), 3.66 (dt, J…

297172-16-8, The synthetic route of 297172-16-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; VERTEX PHARMACEUTICALS, INCORPORATED; WO2006/23852; (2006); A2;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem