1-Methyl-4-piperidone

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The Chinese name N-methyl-4-piperidinone is synonymous with N-methyl-4-piperidinone; 1-Methyl-4-pyridine; 1-Methyl-4-pyridone, 98%; N-methyl-4-piperidinone (cold storage); N-methyl piperidone; N-methyl-2-piperidinone; 1-Methyl-4-pyridone; 1-Methyl-4-piperidine English name 1-Methyll-4-piperidine English synonym 1-METHYL-4-PIPERIDONE; 1-METHYL-4-PIPERIDINONE; 1-METHYLTETRAHYDROPYRIDIN-4(1H)-ONE; N-METHYLPIPERIDONE; N-METHYL-GAMMA-PIPERIDONE; N-METHYL-4-PIPERIDONE; AKOSBBS-00004237; 4-PIPERIDINONE, 1-METHYL-CAS No. 1445-73-4 Molecular formula C6H11NO Molecular weight 113.16 EINECS No. 215-895-5 Related category chemical linkage; Piperidine; Ketones; Pharmaceutical intermediates; Chemical raw material-1; intermediate; Heterocyclic compounds; Piperidone derivatives; Analgesic and anti-inflammatory drugs; Medical analgesics and anti-inflammatory drugs; PHARMACEUTICALINTERMEDIATES; AminesandAnilines; CarbonylCompounds; Amines and anilines; Carbonyl compounds; Miscellaneous; Piperidines,Piperidones,Piperazines; Piperidine; BuildingBlocks; HeterocyclicBuildingBlocks; Piperidones; Heterocycles; MiscellaneousReagents; Piperidine series; pharmaceutical; Raw materials; Intermediate - organic intermediate; Organic chemical raw materials; Chemical raw materials; Organic intermediates; Thiadiazoles; 1445-73-4Mol file 1445-73-4. mol structural formula N-methyl-4-piperidinone properties melting point 192-193 ° C (Solv: ethyl acetate (141-78-6)) boiling point 55-60 ° C11mmHg (lit.) density 0.92g/mL at 25 ° C (lit.) refractive index n20/D1.460 flash point 140 ° F storage conditions Storebelt+30 ° C. Solubility soluble in chloroform (small amount), ethyl acetate (small amount), methanol (small amount) acidity coefficient (pKa) 8.02 ± 0.20 (predicted) form liquid color transparent yellow to orange specific gravity 0.92PH value 12 (100g/l, H2O, 20 ° C) water solubility Miscible sensitivity AirSensitive BRChemicalbook 106924CAS database 1445-73-4 (CASData Base Reference) NIST chemical substance information 4-Piperidinone, 1-methyl - (1445-73-4) N-methyl-4-piperidinone Application and synthesis method introduction N- Methyl-4-piperidone is an important pharmaceutical intermediate. Due to its highly reactive carbonyl group, the methyl group has some special pharmacological effects and is smaller in size compared to other alkyl groups, making it easier to bind with other pharmaceutical functional groups. It has a wide range of applications in drug synthesis, such as the painkiller piprazole, asthma drug ketotifen, 5-hydroxytryptamine antagonist thiamethoxam, and anti allergic drugs such as diphenylamine, selegiline, azatadine, piperidophylline, mehexidine, piperidone maleate, and imipin. It is also widely used in the synthesis of heterocyclic pesticides. It has a wide range of applications in drug synthesis, such as the painkiller piprazole ketone, asthma drug ketotifen, 5-hydroxytryptamine antagonist thiamethoxam, anti allergic drugs such as diphenylamine, cyproheptadine, azatadine, piperidone, mequat, piperidone maleate, and imipin. It is also widely used in the synthesis of heterocyclic pesticides. N-methyl-4-piperidinone was synthesized from methyl acrylate and methylamine gas through Michael addition, Dieckmann cyclization, and decarboxylation reactions. Operation method: (1) Synthesis of N, N-bis (β - methyl acrylate) methylamine (II). Add 180g (2.09mol) of methyl acrylate (containing a polymerization inhibitor) to a 250mL four necked reaction flask. Start stirring and reduce the amount by introducing dry methylamine gas. Control the gas flow rate at 3.0-3.5g/h and the temperature at 30-35 ℃. Introduce 35g (1.13mol) of methylamine gas. After ventilation, keep the reaction at room temperature for 2 hours. Distillation of methyl acrylate is carried out at atmospheric pressure. When the temperature reaches 90 ℃, vacuum distillation is performed to collect 195g (II) of the product with a yield of 92%. (2) The synthesis of N-methyl-4-piperidone (I) was carried out in a 500mL four necked reaction flask with stirring and distillation apparatus, and 120g (134mL) of toluene was added. Add 16g (0.30mol) of solid sodium methoxide while stirring, raise the temperature to 70 ℃, and add 60g (I) (0.3mol). Continue to heat up the reaction, stop heating when the temperature reaches 105 ℃, react for 2 hours, and the cyclization reaction ends. Methanol and toluene will evaporate during the reaction process. Cool down to 0 ℃, add 250mL of 18% hydrochloric acid, control the temperature at 10-15 ℃, measure pH=1, and let it stand for stratification. Extract the toluene layer again with 40mL concentrated hydrochloric acid, combine the hydrochloric acid layers, heat up and reflux the reaction for 5 hours, complete the decarboxylation reaction, and use TLC analysis to determine the endpoint of the reaction. Cool down to room temperature, add 40% sodium hydroxide solution dropwise, adjust the pH to 12-13, and then extract with dichloromethane in three separate extractions, with dichloromethane dosages of 150, 100, and 50 mL. Combine the dichloromethane extracts, first evaporate the dichloromethane at atmospheric pressure, then distill it under reduced pressure (20 mmHg), collect the fraction at 65-75 ℃, and obtain 21.4g (I) of product with a yield of 64%.