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| | 4-Chloro-N-methylpiperidine Basic information |
| | 4-Chloro-N-methylpiperidine Chemical Properties |
| Melting point | 160-165°C | | Boiling point | 162°C(lit.) | | density | 1.02 | | vapor pressure | 3.493hPa at 25℃ | | refractive index | 1.4670-1.4710 | | Fp | 48 °C | | storage temp. | Inert atmosphere,Room Temperature | | solubility | Chloroform (Slightly), Ethanol (Slightly) , Methanol (Slightly) | | form | clear liquid to slightly cloudy liquid | | pka | 7.88±0.10(Predicted) | | color | Colorless to Light yellow to Light orange | | Water Solubility | 1.533g/L at 29℃ | | InChIKey | MYGXGCCFTPKWIH-UHFFFAOYSA-N | | LogP | 1.318 at 25℃ | | CAS DataBase Reference | 5570-77-4(CAS DataBase Reference) | | EPA Substance Registry System | Piperidine, 4-chloro-1-methyl- (5570-77-4) |
| | 4-Chloro-N-methylpiperidine Usage And Synthesis |
| Chemical Properties | Clear colorless liquid | | Uses | 4-Chloro-1-methylpiperidine is a reactant in the synthesis of indole and benzimidazole piperazines as histamine H4 receptor antagonist. | | Flammability and Explosibility | Not classified | | Synthesis | To an anhydrous tetrahydrofuran (THF, 7 mL) solution of diisopropylamine (1.078 mL) was slowly added n-butyllithium (3.08 mL, 2.5 M) dropwise at 0 °C. The reaction solution was stirred at 0 °C for 40 min and then cooled to -23 °C. Subsequently, N-methyl-2-piperidone (0.80 mL) was added to the reaction system and stirred at -23°C for 0.5 hr, after which stirring was continued at -78°C for 1 hr. Next, a solution of anhydrous THF (14 mL) of 4-chloromethyl-N-tritylimidazole (2.70 g) was added dropwise to the above mixture. The reaction mixture was stirred at -78 °C for 4 hours, followed by slow warming to room temperature and stirring overnight (16 hours). Upon completion of the reaction, water and ethyl acetate were added to the mixture and the organic layer was separated after vigorous shaking. The aqueous layer was extracted several times with ethyl acetate and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to give the crude product. The crude product was purified by fast chromatography (eluent: dichloromethane solution of saturated methanol with 1% to 2% ammonia) to afford the target compound N-methyl-4-chloropiperidine (1.58 g, 52% yield). | | Physiological effects | 4-Chloro-N-methylpiperidine can be used to treat bronchial asthma, chronic obstructive pulmonary disease, and other respiratory disorders by inhibiting the production of histamine in the body. It also has antihistaminic effects that may be due to its ability to inhibit histamine release from mast cells or block H1 receptors. | | References | [1] Patent: US5932596, 1999, A
[2] Patent: US5807872, 1998, A |
| | 4-Chloro-N-methylpiperidine Preparation Products And Raw materials |
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