Preparing process of arecoline and its analog
A technology of arecoline and toluene, applied in the direction of organic chemistry, etc., can solve the problems of long process route, expensive methyl iodide, high processing cost, etc., and achieve good reaction effect and simple operating conditions
Active Publication Date: 2009-08-19
SUZHOU WELLBRIDGE BIOLOGICAL TECH CO LTD
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Problems solved by technology
[0009] However, there are still many defects in the main route for preparing arecoline or its analogs in the prior art. One is that the process route is too long, and each process needs to be strictly handled. The other is that in the N-methylation process, it needs The use of more expensive methyl iodide makes the processing cost of the product relatively high
Method used
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Embodiment 1
[0032] Add 50g (0.406mol) of nicotinic acid and 45.2g (0.447mol) of triethylamine into 500ml of toluene, raise the temperature to 70°C, add 112.6g (0.894mol) of dimethyl sulfate dropwise at this temperature, after the addition is complete, raise the temperature to 100 °C, react for 3Hr, and cool to room temperature. Since the hydroboration reaction is carried out in benzene and water mixed solution (document J.Org.chem.1955, 1761-1766), the reactants of the previous step need not be processed to obtain pure N-methyl nicotinic acid methyl ester or N- Methyl nicotinate monomethyl sulfate can be used for hydroboration reaction. Add 500ml of water to the system formed after the above reaction, and add 31g of NaBH at 35-38°C 4 (0.82mol), add in batches for about 1 hr, and react at room temperature for 4 hours after the addition. The whole reaction process is shown in formula VIII.
[0033]
[0034] (Formula VIII)
[0035] Then stand for stratification, the organic phase is t...
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The invention provides a preparation method of arecoline or its analogs. In the presence of an organic base, the reaction raw materials such as nicotinic acid are simultaneously esterified and alkylated with a compound that can provide an alkyl group in an organic solvent, and then undergo a reduction reaction and post-treatment to obtain arecoline or its analogues. thing. The invention combines the two processes of esterification and N-methylation into one, shortening the process route for preparing arecoline or its analogues. The method has simple operating conditions and convenient intermediate treatment; the reaction raw materials can avoid higher-priced halogenated alkanes (such as methyl iodide), and use lower-priced sulfuric acid esters or phosphoric acid ester compounds, which also have good implementation effects, and the resulting product is more efficient. With cost advantage.
Description
technical field [0001] The invention relates to a preparation method of arecoline or arecoline analogues, belonging to the technical field of chemical synthesis. technical background [0002] Arecoline (Arecoline) chemical name is "N-methyl-1,2,5,6-tetrahydronicotinic acid methyl ester", its structure is shown in formula I, it is a kind of M, N receptor agonist, It has an anticholinergic effect on the central nervous system and can also be used as a raw material for the synthesis of other M receptor agonists. Therefore, arecoline is a compound with great application value, and its preparation method has always been paid attention to by people. [0003] U.S. Patent No. 2506458 introduced the synthesis method of arecoline earlier, which uses 3,3'-iminodipropionitrile as a raw material, and is prepared through steps such as N-methylation, nitrilation, condensation cyclization, and catalytic hydrogenation. Arecoline. This method has rare raw materials and complicated preparat...
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IPC IPC(8): C07D211/78
Inventor 严兵顾善修顾瑜
Owner SUZHOU WELLBRIDGE BIOLOGICAL TECH CO LTD