Downstream synthetic route of 122860-33-7

122860-33-7 Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate 736490, apiperidines compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.122860-33-7,Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate,as a common compound, the synthetic route is as follows.

26c. Phenylmethyl 4-formylpiperidinecarboxylate To a stirred solution of oxalyl chloride (2M solution in dichloromethane, 10.9 mL, 21.9 mmol) was added DMSO (3.1 mL, 3.4 g, 43.8 mmol) in dichloromethane (6 mL) over a period of 15 minutes. The product of Example 26b (4.4 g, 17.5 mmol) in dichloromethane (7 mL) was then added at -78 C. over a period of 15 minutes. The resultant solution was stirred at -78 C. for 1 hour and then triethylamine (12.2 mL, 8.86 g, 87.5 mmol) was added, dropwise, over a period of 15minutes. The mixture was further stirred at -78 C. for 30 min and then at 0 C. for 15 min. The reaction mixture was quenched with water and extracted with dichloromethane. The combined organic phase was washed with 1% HCl, water, dried over sodium sulfate, filtered and evaporated to give the title compound (4.4 g, 100%) which was used in the next step without purification. 1H NMR (300 MHz, CDCl3) delta9.65 (s, 1H), 7.28-7.38 (m, 5H), 5.12 (s, 2H), 4.04 (br d, J=13.1 Hz, 2H), 2.97-3.06 (m, 2H), 2.38-2.45 (m, 1H), 1.88-1.92 (m,2H), 1.52-1.64 (m, 2H). 13C NMR (75 MHz, CDCl3) delta202.7, 155.2, 136.7, 128.5, 128.6, 127.9, 67.2, 47.8, 43.0, 25.1. LRMS (APIMS) m/z 248 (MH+)., 122860-33-7

122860-33-7 Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate 736490, apiperidines compound, is more and more widely used in various fields.

Reference:
Patent; Fang, Xinqin; Garvey, David S.; Gaston, Ricky D.; Lin, Chia-En; Ranatunga, Ramani R.; Richardson, Stewart K.; Wang, Tiansheng; Wang, Weiheng; Wey, Shiow-Jyi; US2003/203915; (2003); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

 

Analyzing the synthesis route of 122860-33-7

As the paragraph descriping shows that 122860-33-7 is playing an increasingly important role.

122860-33-7, Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 3 4-Bromomethylpiperidine-1-carboxylic Acid Benzyl Ester To a solution of 4-hydroxymethylpiperidine-1-carboxylic acid benzyl ester (1.11 g), carbon tetrabromide (1.77 g) in methylene chloride (11 ml) was added triphenylphosphine (1.4 g) with ice-cooling, and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, the solvent was evaporated and the obtained residue was purified by silica gel column chromatography (hexane:acetone=10:1) and dried under reduced pressure to give the title compound (1.25 g). 1H-NMR (delta ppm, CDCl3) 1.05-1.30 (m, 2H), 1.70-1.90 (m, 3H), 2.78 (m, 2H), 3.29 (d, 2H), 4.10-4.30 (m, 2H), 5.13 (s, 2H), 7.26-7.38 (m, 5H)., 122860-33-7

As the paragraph descriping shows that 122860-33-7 is playing an increasingly important role.

Reference:
Patent; Japan Tobacco Inc.; US6562828; (2003); B1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

 

Downstream synthetic route of 122860-33-7

122860-33-7 Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate 736490, apiperidines compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.122860-33-7,Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate,as a common compound, the synthetic route is as follows.

Reaction Step 2 Synthesis of benzyl 4-formylpiperidine-1-carboxylate To a stirred solution of benzyl 4-(hydroxymethyl)piperidine-1-carboxylate (10.0 g, 40.2 mmol, 1.0 eq) in dichloromethane (150 ml), Dess-Martin periodinane (20.4 g, 48.2 mmol, 1.2 eq) was added at 0 C. and stirring was continued at room temperature for 12 h. After completion of the reaction (monitored by TLC, 30% ethyl acetate-hexane, Rf=0.45), the mixture was diluted with dichloromethane and washed with saturated sodium bicarbonate solution, followed by brine. The organic extract was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (100-200 mesh), eluting with a 30-40% gradient of ethyl acetate in hexanes to obtain benzyl 4-formylpiperidine-1-carboxylate (6.2 g, 62.5%). LCMS Purity: 78.54% (ES+): m/z 248.27 (M+H+); tr=3.01 min., 122860-33-7

122860-33-7 Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate 736490, apiperidines compound, is more and more widely used in various fields.

Reference:
Patent; INNOV17 LLC; Gaweco, Anderson; Tilley, Jefferson; Blinn, James; (68 pag.)US2016/24056; (2016); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem