Category: 280774-03-0

280774-03-0, (1-Isopropylpiperidin-4-yl)methanol is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To the product from step 1 Example 139 (115 mg, 0.55 mmol) in DMSO (5 mL) was added (1-isopropanol-piperidin-4-yl)methanol (130 mg, 0.83 mmol) and 1M KtOBu (1.1 mL, 1.1 mmol). After overnight stirring at 100 C., the reaction was diluted with dichloromethane, washed with water/brine several times, dried over sodium sulfate, and concentrated. The product was purified by prep TLC plates to obtain 64 mg (35%); Mp 188-191 C.; MS m/z 329 (M+H).

280774-03-0, The synthetic route of 280774-03-0 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Cephalon, Inc.; US2008/27041; (2008); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

280774-03-0, (1-Isopropylpiperidin-4-yl)methanol is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step D: (4-Chloro-phenyl)-[2-(1-isopropyl-piperidin-4-ylmethoxy)-3-methyl-3H-imidazol-4-yl]-methanone. To a 1-L, three-necked, round-bottomed flask equipped with a magnetic stirrer, nitrogen inlet and an addition funnel was added NaH (1.45 g, 0.061 mol) and THF (300 mL). The stirred suspension was cooled to 0 C. and (1-isopropyl-piperidin-4-yl)-methanol (9.5 g, 0.06 mol) was added. The cooling bath was removed, and the reaction warmed to rt. After 2 h, a solution of (2-chloro-3-methyl-3H-imidazol-4-yl)-(4-chloro-phenyl)-methanone (15.56 g, 0.061 mol) in dry THF (100 mL) was added. The reaction mixture was stirred at 60 C. and monitored by HPLC every 4-8 h. After 36 h, the reaction was judged complete. The reaction mixture was cooled to rt, poured into ice-cold water, and extracted with EtOAc (2*250 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure to provide the crude material as a brown solid. Recrystallization from EtOAc afforded the desired product (17.5 g, 78%) as a white crystalline solid. mp 126-127 C. IR (film): 2963, 1615, 1585, 1529, 1481, 1362, 1287, 1213, 1173, 1104, 1020, 897, 846, 727, 698 cm-1. 1H NMR (400 MHz, CDCl3): delta7.67 (d, J=8.6 Hz, 2H), 7.38 (d, J=8.6 Hz, 2H), 7.13 (s, 1H), 4.22 (d, J=6.0 Hz, 2H), 3.68 (s, 3H), 2.84 (m, 2H), 2.61 (m, 1H), 2.09 (m, 2H), 1.74 (m, 3H), 1.30 (m, 2H), 0.97 (d, J=6.5 Hz, 6H). 13C NMR (100 MHz, CDCl3): delta183.4, 157.0, 138.3, 138.2, 137.3, 130.2, 128.7, 127.1, 74.9, 54.6, 48.4, 35.9, 30.7, 29.1, 18.3. HRMS (EI): m/z calcd for C20H27ClN3O2 [M+H]+, 376.1792; found, 376.1801. Anal. Calcd for C20H26ClN3O2: C, 63.91; H, 6.97; N, 11.17. Found: C, 63.55; H, 6.77; N, 11.05.

280774-03-0, The synthetic route of 280774-03-0 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Jones, Todd K.; Mani, Neelakandha; US2005/250948; (2005); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

280774-03-0, (1-Isopropylpiperidin-4-yl)methanol is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step A. 4-{5-[(3-Fluoro-phenyl)-(tert-butyl-dimethyl-silanyloxy)-methyl]-1-methyl-1H-imidazol-2-yloxymethyl}-1-isopropyl-piperidine. To a 0 C. solution of (1-isopropyl-piperidin-4-yl)-methanol (1 equiv.) in THF (0.1 M) is added NaH (1.01 equiv.). The cooling bath is removed, and the reaction is warmed to rt. After 2 h, a solution of 5-[(3-fluoro-phenyl)-(tert-butyl-dimethyl-silanyloxy)-methyl]-2-chloro-1-methyl-1H-imidazole (1.01 equiv.) in dry THF (0.6 M) is added. The reaction mixture is then heated to 60 C. Upon completion of the reaction, mixture is cooled to rt, poured into ice-cold water, and extracted with EtOAc. The combined organic extracts are dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure to provide the crude material. The crude material is purified by chromatography or recrystallization

280774-03-0, As the paragraph descriping shows that 280774-03-0 is playing an increasingly important role.

Reference：
Patent; Jones, Todd K.; Mani, Neelakandha; US2005/250948; (2005); 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.280774-03-0,(1-Isopropylpiperidin-4-yl)methanol,as a common compound, the synthetic route is as follows.

D. 1-Isopropylpiperidine-4-carboxaldehyde A solution of 1-isopropylpiperidine-4-methanol (0.40 g, 2.5 mmol) and N-methylmorpholine (0.46 g, 3.8 mmol) in methylene chloride (20 mL) was treated with tetrapropylammonium perruthenate (0.089 g, 0.25 mmol). After 3 h, the mixture was concentrated and the residue purified by column chromatography (SiO2: 10% to 20% methanol:methylene chloride) affording 0.20 g (50%) of the title compound. 1NMR; FIA-MS, m/e 156 (m+)., 280774-03-0

The synthetic route of 280774-03-0 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Eli Lilly and Company; US6635657; (2003); B1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

280774-03-0, (1-Isopropylpiperidin-4-yl)methanol is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Reference Example 2 Oxalyl chloride (3.15 ml) was dissolved in 30 ml of dichloromethane, a solution of 3.20 ml of dimethyl sulfoxide in 6 ml of dichloromethane was added thereto at-70?C, the mixture was stirred for 15 minutes, a solution of 2.93 g of (1-isopropyl-4-piperidyl)methanol in 15 ml of dichloromethane was added thereto at -70?C and the mixture was stirred for 1 hour. After 12.5 ml of triethylamine were added at -70?C, the mixture was raised to room temperature, then water and a saturated aqueous solution of sodium hydrogen carbonate were added and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated in vacuo and ethyl acetate was added to the resulting residue. After removing the insoluble matter by filtration, the solvent was evaporated in vacuo to give 1.15 g of 1-isopropylpiperidine-4-carbaldehyde. This compound was used for the next reaction without purification.

280774-03-0, 280774-03-0 (1-Isopropylpiperidin-4-yl)methanol 11147855, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; YAMANOUCHI PHARMACEUTICAL CO. LTD.; EP1336605; (2003); 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.280774-03-0,(1-Isopropylpiperidin-4-yl)methanol,as a common compound, the synthetic route is as follows.

Step D: Preparation of (4-Chlorophenyl)-[2-(1-isopropyl-piperidin-4-ylmethoxy)-3-methyl-3H-imidazol-4-yl]-methanone. (1-Isopropyl-piperidin-4-yl)-methanol (0.08 g) in THF (10 mL) was treated with NaH (60% in mineral oil, 0.02 g). After 30 min, the reaction mixture was cooled to 0 C. and the product of Example V, Step C (0.125 g) in THF (5 mL) was added. After stirring overnight, the reaction mixture was partitioned between brine and EtOAc. The organic portion was separated, washed twice with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography with silica gel using a gradient elution of 1-4% MeOH in CH2Cl2 to provide (4-Chloro-phenyl)-[2-(1-isopropyl-piperidin-4-ylmethoxy)-3-methyl-3H-imidazol-4-yl]-methanone (0.07, 51 %) as a white solid. M calc=375; M+H found=376. 1H NMR (400 MHz, CDCl3): delta7.66 (d, J=8.3 Hz, 2H), 7.37 (d, J=8.6 Hz, 2H), 7.13 (s, 1H), 4.24 (d, J=6.1Hz, 2H), 3.69 (s, 3H), 2.88 (br d, J=11.0 Hz, 2H), 2.69 (m, 1H), 2.12 (br dd, J=12.6, 9.6 Hz, 2H), 1.88-1.69 (br m, 1H), 1.37 (br dd (J=23.2, 9.3 Hz, 2H), 0.99 (d, J=6.6 Hz, 6H), 280774-03-0

280774-03-0 (1-Isopropylpiperidin-4-yl)methanol 11147855, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Jones, Todd K.; Mani, Neelakandha; US2005/250948; (2005); 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.280774-03-0,(1-Isopropylpiperidin-4-yl)methanol,as a common compound, the synthetic route is as follows.

A microwave vial was charged with l-(6-methoxy-5-methylpyridin-3-yl)-4,5,7,8-tetrahydro-lH- oxepino[4,5-c]pyrazol-3-ol (51 mg, 0.185 mmol), (1 -isop ropyl p i per id i n-4-yl)methanol (68 mg, 0.411 mmol) and 2-(tributylphosphoranylidene)acetonitrile (0.143 ml_, 0.547 mmol). The vial was sealed and degassed with nitrogen. Anhydrous toluene (2.5 mL) was added to the reaction mixture which was then heated in a microwave at 120 C for 1 h. The reaction mixture was treated with further (1- isopropylpiperidin-4-yl)methanol (50 mg, 0.302 mmol) and 2-(tributylphosphoranylidene)acetonitrile (0.143 mL, 0.547 mmol) and the reaction mixture was heated at 120 C for 1 h. The reaction mixture was concentrated under a stream of nitrogen and the residue was taken up in water (5 mL) and partitioned with EtOAc (5 mL). The aqueous layer was extracted with further EtOAc (3 x 5 mL) and the combined organic layer wsa passed through a hydrophobic frit and concentrated under reduced pressure. The crude product was purified by MDAP (Method A) to give the title compound (15 mg, 17%). LCMS (Method A) : Rt = 0.66 min, MH+ = 415. 1H NMR (400 MHz, MeOD) delta ppm 8.56 (br. s., 1H), 7.95 (br. s., 1H), 7.51 (br. s., 1H), 4.09 (d, J=5 Hz, 2H), 3.99 (s, 3H), 3.80 (dt, J=15, 5 Hz, 4H), 3.50-3.32 (m, 3H), 2.98 (t, J=12 Hz, 2H), 2.81 (t, J=4 Hz, 2H), 2.74-2.60 (m, 3H), 2.23 (s, 3H), 2.07 (d, J=14 Hz, 2H), 1.81-1.59 (m, 2H), 1.33 (d, J=6 Hz, 6H), 280774-03-0

As the paragraph descriping shows that 280774-03-0 is playing an increasingly important role.

Reference：
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BAXTER, Andrew; BERTRAND, Sophie Marie; CAMPBELL, Matthew; DOWN, Kenneth David; HAFFNER, Curt Dale; HAMBLIN, Julie Nicole; HENLEY, Zoe Alicia; MILLER, William Henry; TALBOT, Eric Philippe Andre; TAYLOR, Jonathan Andrew; (325 pag.)WO2018/192864; (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.280774-03-0,(1-Isopropylpiperidin-4-yl)methanol,as a common compound, the synthetic route is as follows.

(1) Lithium aluminum hydride (1.10 g) is suspended in tetrahydrofuran (80 ml), and thereto is added a solution of ethyl 1-isopropylpiperidine-4-carboxylate (5.00 g) obtained in Reference Example 127 in tetrahydrofuran (30 ml) dropwise under ice-cooling. The reaction solution is stirred for 2 hours under the ice-cooling, and water (1.1 ml), 15 % aqueous sodium hydroxide solution (1.1 ml) and water (3.3 ml) are added dropwise successively and stirred for additional 10 minutes. To the resulting reaction solution is added potassium carbonate, and the mixture is stirred for 20 minutes, and then the insoluble materials are removed by filtration. The filtrate is concentrated under reduced pressure, and then the resulting residue is purified by NH-silica gel column chromatography (eluent: chloroform/ethyl acetate = 1/1) to give (1-isopropylpiperidin-4-yl)methanol (4.29 g). APCI-MS M/Z:158[M+H]+.(2) Oxalyl chloride (2.0 ml) is dissolved in dichloromethane (120 ml) and thereto is added dropwise a solution of dimethylsulfoxide (3.3 ml) in dichloromethane (15 ml) under dry ice-acetone cooling. After stirring for 10 minutes under ice-cooling, a solution of (1-isopropylpiperidin-4-yl)methanol (3.00 g) obtained in Reference Example 134(1) in dichloromethane (30 ml) is added dropwise over a period of 15 minutes. After addition, the reaction solution is stirred for 2 hours under ice-cooling, and thereto is added dropwise triethylamine (13.3 ml) over a period of 10 minutes. The reaction solution is stirred for one hour while it is warmed to room temperature, and then the solution is poured to saturated aqueous sodium hydrogen carbonate solution. The mixture is extracted with dichloromethane and evaporated to remove the solvent under reduced pressure. The aqueous layer is extracted with ethyl acetate, and the extract is combined with the residue obtained by removing solvent from the above dichloromethane-extract, washed with water and saturated brine and dried over sodium sulfate. The solvent is evaporated under reduced pressure to give the crude material, 1-isopropylpiperidine-4-carbaldehyde (1.96 g). APCI-MS M/Z:156[M+H]+.(3) Triethyl phosphonoacetate (7.96 g) is dissolved in tetrahydrofuran (50 ml) and thereto is added gradually 60 % sodium hydride in oil (1.45 g) under ice-cooling. After stirring for 20 minutes under ice-cooling, to the mixture is added 1-isopropylpiperidine-4-carbaldehyde (5.03 g) obtained in Reference Example 134(2) in tetrahydrofuran (25 ml). The reaction solution is stirred for 3 hours, diluted with diethyl ether, thereto is added water and the mixture is extracted with ethyl acetate. The organic layer is washed with water and saturated brine, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate = 9/1) to give ethyl 3-(1-isopropylpiperidin-4-yl)acrylate (6.87 g). APCI-MS M/Z:226[M+H]+.(4) Ethyl 3-(1-isopropylpiperidin-4-yl)acrylate (1.01 g) obtained in Reference Example 134(3) is dissolved in ethanol (20 ml), thereto is added 2 N aqueous sodium hydroxide solution (4.5 ml) and the mixture is stirred at room temperature for 24 hours. To the reaction solution is added 2 N hydrochloric acid (9 ml), and the mixture is concentrated under reduced pressure, and then the resulting residue is lyophilized to give the title compound (1.43 g). APCI-MS M/Z:198[M+H]+., 280774-03-0

280774-03-0 (1-Isopropylpiperidin-4-yl)methanol 11147855, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; Tanabe Seiyaku Co., Ltd.; EP1489078; (2004); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem