Some tips on 22065-85-6

22065-85-6 1-Benzylpiperidine-4-carbaldehyde 89584, apiperidines compound, is more and more widely used in various fields.

22065-85-6, 1-Benzylpiperidine-4-carbaldehyde is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 20 Production of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidene]methylpiperidine using a mixed solvent of methanol and toluene and sodium hydroxide and adopting method A Into a 50-mL four-necked flask were charged 2.0 g (10.4 mmol) of 5,6-dimethoxy-1-indanone, 2.5 g (12.3 mmol, 1.2 equivalents) of 1-benzyl-4-formylpiperidine and 24 mL of a mixed solvent (methanol: toluene = 16: 14). After the air in the system was replaced with nitrogen, 0.5 g (12.5 mmol, 1.2 equivalents) of sodium hydroxide was added to the reaction solution with refluxing (65C). After completion of the addition, stirring was continued with refluxing for 1 hour to complete the reaction. Then, the reaction solution was air-cooled until crystals were precipitated. After the precipitation, the reaction solution was further cooled (cooling rate: 36C/hour) and the crystals precipitated at 4C or higher were collected by filtration. The crystals began to be precipitated at 49C. The crystals collected by filtration were washed with water (30 mL) and 6 mL of methanol and dried at 50C (drying time: 2 hours and 35 minutes) to obtain 3.31 g of the crystals of the title compound (yield: 84.3%). 1H-NMR data of these crystals agreed with those obtained in Example 1., 22065-85-6

22065-85-6 1-Benzylpiperidine-4-carbaldehyde 89584, apiperidines compound, is more and more widely used in various fields.

Reference£º
Patent; Eisai R&D Management Co., Ltd.; EP1911745; (2008); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

 

Analyzing the synthesis route of 22065-85-6

The synthetic route of 22065-85-6 has been constantly updated, and we look forward to future research findings.

22065-85-6, 1-Benzylpiperidine-4-carbaldehyde is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

3-3) 1-Benzyl-4-[(5,6-diethoxy-1-indanon)-2-ylidene]methylpiperidine To a solution of 24.1 g of 5,6-diethoxy-1-indanone in 70 ml of THF was added 26.7 g of 1-benzyl-4-formylpiperidine in 100 ml of THF, followed by addition of a solution of 23.2 g of sodium methoxide (28% methanol solution) in 30 ml of THF under ice-cooling. After stirring for 2 hours as it was, the mixture was poured onto ice water, and the precipitated solid was collected by filtration and dried. The product was recrystallized from ethyl acetate-ethanol, to give 39.6 g (89%) of the title compound as white crystals., 22065-85-6

The synthetic route of 22065-85-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Eisai Co., Ltd.; EP1468684; (2004); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

 

Simple exploration of 22065-85-6

22065-85-6, 22065-85-6 1-Benzylpiperidine-4-carbaldehyde 89584, apiperidines compound, is more and more widely used in various.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.22065-85-6,1-Benzylpiperidine-4-carbaldehyde,as a common compound, the synthetic route is as follows.

Example 1: Preparation of 2-[(E)-l-(l-benzyl-4-piperidyl)methylidene] -5,6-dimethoxy-l-indanone compound[62] 20 g of 5,6-dimethoxy-l-indanone and 23.27 g of l-benzyl-piperidine-4-carbaldehyde were added to 200 ml of tetrahydrofuran, and 6.75 g of sodium methoxide was added dropwise at 0 to 1O0C under nitrogen current. The resulting mixture was stirred at 0 to 1O0C for 15 minutes, and slowly warmed to a temperature of 20 to 250C and stirred for 3 hours. 160 ml of dichloromethane and 100 ml of purified water were added to the reaction mixture, and then adjusted to a pH range of 9.5 to 9.8 with 20% HCl. Then an organic phase was separated and distilled to remove a solvent. 60 ml of methanol was added to the residue, stirred at reflux for one hour, cooled to a temperature of 0 to 1O0C, and stirred for one hour. The resulting mixture was filtered, washed, and dried under a vacuum condition to obtain 36.53 g of a target compound (yield: 93.0%).[63] m.p. 175-1770C;[64] m/e 377.5 (parent ion);[65] 1U NMR (CDCl ) deltal.62~1.83 (m, 4H), 2.08-2.26 (m, 2H), 2.27-2.42 (m, IH),2.92-3.03 (m, 2H), 3.55-3.67 (m, 4H), 3.92 (s, 3H), 3.97 (s, 3H), 6.65 (d, IH), 6.89 (s, IH), 7.28 (s, IH), 7.30-7.39 (m, 5H) Example 2: Preparation of 2-[(E)-l-(l-benzyl-4-piperidyl)methylidene] -5,6-dimethoxy-l-indanone compound[68] 20 g of 5,6-dimethoxy-l-indanone and 23.27 g of l-benzyl-piperidine-4-carbaldehyde were added to 200 ml of tetrahydrofuran, and 8.50 g of sodium methoxide was added dropwise at 0 to 1O0C under nitrogen current. The resulting mixture was stirred at 0 to 1O0C for 15 minutes, and slowly warmed to a temperature of 20 to 250C and stirred for 3 hours. 160 ml of dichloromethane and 100 ml of purified water were added to the reaction mixture, and then adjusted to a pH range of 9.5 to 9.8 with 20% HCl. Then an organic phase was separated and distilled to remove a solvent. 60 ml of methanol was added to the residue, stirred at reflux for one hour, cooled to a temperature of 0 to 1O0C, and stirred for one hour. The resulting mixture was filtered, washed, and dried under a vacuum condition to obtain 33.86 g of a target compound (yield: 86.2%).

22065-85-6, 22065-85-6 1-Benzylpiperidine-4-carbaldehyde 89584, apiperidines compound, is more and more widely used in various.

Reference£º
Patent; DONG WHA PHARM. IND. CO., LTD.; WO2008/126995; (2008); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

 

Downstream synthetic route of 22065-85-6

22065-85-6 1-Benzylpiperidine-4-carbaldehyde 89584, apiperidines compound, is more and more widely used in various.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.22065-85-6,1-Benzylpiperidine-4-carbaldehyde,as a common compound, the synthetic route is as follows.

Example 11 Production of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidene]methylpiperidine using a mixed solvent of 2-propanol and toluene and sodium methoxide and adopting method A Into a 50-mL four-necked flask were charged 2.0 g (10.4 mmol) of 5,6-dimethoxy-1-indanone, 2.5 g (12.3 mmol, 1.2 equivalents) of 1-benzyl-4-formylpiperidine and 24 mL of a mixed solvent (2-propanol: toluene = 16: 14). After the air in the system was replaced with nitrogen, 2.4 g (12.4 mmol, 1.2 equivalents) of a 28%-sodium methoxide/methanol solution was poured into the reaction solution with refluxing (83C). After completion of the pouring, stirring was continued with refluxing for 1 hour and 2 minutes to complete the reaction. Then, the reaction solution was cooled to 7C (cooling rate: 33C/hour). Crystals began to be precipitated at 42C. The crystals were collected by filtration, washed with water (30 ml) and 6 mL of methanol and then dried at 50C (drying time: 1 hour and 20 minutes) to obtain 2.87 g of the crystals of the title compound (yield: 73.1%). 1H-NMR data of these crystals agreed with those obtained in Example 1.

22065-85-6 1-Benzylpiperidine-4-carbaldehyde 89584, apiperidines compound, is more and more widely used in various.

Reference£º
Patent; Eisai R&D Management Co., Ltd.; EP1911745; (2008); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

 

Brief introduction of 22065-85-6

The synthetic route of 22065-85-6 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.22065-85-6,1-Benzylpiperidine-4-carbaldehyde,as a common compound, the synthetic route is as follows.

To a cooled solution of 1-benzyl-4-piperidinecarboxaldehyde (407 mg, 2.0 mmol) and propargylamine (165 mg, 3.0 mmol) in MeOH (6 mL) at 0 C, a small amount of CF3CO2H (5 drops) was added. After being stirred for 1 h, NaBH3CN (189 mg, 2.9 mmol) was added to the solution portionwsise. The mixture was stirred at rt overnight and then quenched with aqueous saturated NaHCO3. The mixture was concentrated in vacuo and then extracted with AcOEt.

The synthetic route of 22065-85-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Universitat Autonoma de Barcelona; Consejo Superior de Investigaciones Cientificas (CSIC); National University Corporation Okayama University; Universidad de Alcala; Esteban, Gerard; Unzeta, Mercedes; Inokuchi, Tsutomu; Marco-Contelles, Jose Luis; Samadi, Abdelouahid; Iriepa, Isabel; Ojima, Masaki; Li, Wang; EP2727916; (2014); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem