1-Methyl-4-piperidione
1-Methyl-4-piperidone
CAS: 1445-73-4
Molecular Formula: C6H11NO
1-Methyl-4-piperidione - Names and Identifiers
1-Methyl-4-piperidione - Physico-chemical Properties
| Molecular Formula | C6H11NO |
| Molar Mass | 113.16 |
| Density | 0.92 g/mL at 25 °C (lit.) |
| Melting Point | 192-193 °C(Solv: ethyl acetate (141-78-6)) |
| Boling Point | 55-60°C11mm Hg(lit.) |
| Flash Point | 140°F |
| Water Solubility | MISCIBLE |
| Vapor Presure | 0.85mmHg at 25°C |
| Appearance | Liquid |
| Specific Gravity | 0.92 |
| Color | Clear yellow to orange |
| BRN | 106924 |
| pKa | 8.02±0.20(Predicted) |
| PH | 12 (100g/l, H2O, 20℃) |
| Storage Condition | Store below +30°C. |
| Sensitive | Air Sensitive |
| Refractive Index | n20/D 1.460 |
1-Methyl-4-piperidione - Risk and Safety
| Risk Codes | R34 - Causes burns R10 - Flammable R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S23 - Do not breathe vapour. S24/25 - Avoid contact with skin and eyes. S37/39 - Wear suitable gloves and eye/face protection S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| UN IDs | UN 1224 3/PG 3 |
| WGK Germany | 3 |
| HS Code | 29333999 |
| Hazard Note | Irritant |
| Hazard Class | 3 |
| Packing Group | III |
1-Methyl-4-piperidione - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| Introduction | n-methyl-4-piperidone is an important medical intermediate, because of its carbonyl group has high reactivity, methyl group has some special pharmacological effects and compared with other alkyl group is smaller and easier to combine with other pharmaceutical functional groups, which has a wide range of applications in drug synthesis, such as: pain reliever pyrazolone, asthma drug ketotifen, 5-hydroxytryptamine antagonist benzodiazepine, antiallergic drug diphenylaline, segenidine, azatadine, pehaitheophylline, megaline, piriheptadine maleate, bamipin, etc. It is also widely used in the synthesis of Spiro heterocyclic pesticides. |
| Application | has a wide range of applications in the synthesis of drugs, such as: the analgesic pyrazolone, asthma drug ketotifen, 5-hydroxytryptamine antagonist medroxycycline, antiallergic drug diphenylaline, segenidine, azatadine, pehaitheophylline, mehydrorine, piproheptadine maleate, bamipin, etc. It is also widely used in the synthesis of Spiro heterocyclic pesticides. |
| preparation | methyl acrylate and methylamine gas as raw materials, after Michael addition, Dieckmann cyclization, N-methyl -4-piperidone was synthesized by decarboxylation reaction. Methods of operation:(1) synthesis of N,N-bis (methyl β-acrylate) methylamine (II) 180g(2.09mol) of methyl acrylate (containing polymerization inhibitor) was added to a ml Four-necked reaction flask. Start the stirring, reduce the method into the dry methyl amine gas, control the gas flow rate of 3.0~3.5G/h, temperature control at 30~35 ℃, into a methyl amine gas 35g(1.13mol), after the end of ventilation, heat preservation reaction 2H. Methyl acrylate was distilled at atmospheric pressure, and when the temperature reached 90 ° C., vacuum distillation was carried out, and the product was collected to obtain 195g (II) in 92% yield. (2) synthesis of n-methyl-4-piperidone (I) a 500ml four-port reaction bottle was charged with 120g(134ml) of toluene in a stirring and distillation apparatus. Under stirring, 16g(0.30mol) of solid sodium methoxide was added, the temperature was raised to 70 ° C., and 60g (I)(0.3mol) was added. The temperature-raising reaction was continued, and the temperature-raising was stopped when the temperature reached 105 ° C., and the reaction was 2H, and the cyclization reaction was completed. Methanol and toluene were distilled off during the reaction. The temperature was cooled to 0 ° C., 18% of hydrochloric acid was added, the temperature was controlled at 10-15 ° C., pH = 1 was measured, and the layers were separated at rest. The toluene layer was extracted again with 40ml of concentrated hydrochloric acid, and the hydrochloric acid layer was combined. The reaction was heated and refluxed for 5h, and the decarboxylation reaction was completed. The temperature is cooled to room temperature, and 40% sodium hydroxide solution is added dropwise to adjust pH = 12-13, and then extraction is carried out with dichloromethane, and the extraction is divided into 3 times, and the dosage of dichloromethane is 150,100 and 50ml respectively. The dichloromethane extracts were combined, and the dichloromethane was distilled off under normal pressure, and then distilled under reduced pressure (20mmHg) to collect fractions at 65-75 ° C. To obtain 21.4g (I) of the product in a yield of 64%. FIG. 1 is the synthetic route of n-methyl-4-piperidone |
Last Update：2024-04-09 02:00:04
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