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Preparation method of arecoline

A technology of arecoline and organic bases, applied in the direction of organic chemistry, can solve the problems of expensive methyl iodide, high processing costs, long process routes, etc.

Inactive Publication Date: 2016-03-30
QINGDAO KANGYUAN PHARMA
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  • Abstract
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Problems solved by technology

[0005] However, there are still many defects in the main route for preparing arecoline and its analogues 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, The use of more expensive methyl iodide makes the processing cost of the product relatively high

Method used

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  • Preparation method of arecoline

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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 a mixed solution of benzene and water (document J.Org.chem.1955, 1761-1766), the reactant in the previous step does not need to be processed to obtain pure N-methyl nicotinic acid methyl ester or N- Methyl nicotinate monomethyl sulfate can be hydroborated. Add 500ml of water to the system formed after the above reaction, and add 31g of NaBH at 35-38°C 4 (0.82mol), added in batches for about 1 hr, and reacted at room temperature for 4 hours after the addition. The whole reaction process is shown in formula VI:

[0033]

[0034] (Formula VI).

[0035] Then stand for stratification, the organic phase is the tol...

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Abstract

The invention provides a preparation method of arecoline. On the presence of organic base, reaction raw materials such as nicotinic acid and the like have esterification and alkylation reactions with a compound capable of providing alkyl in the organic solvent, and arecoline can be prepared through a reduction reaction and aftertreatment. Two procedures including esterification and N-methylation are combined, and the process route of preparation of arecoline is shortened. According to the method, the operation conditions are simple, and the intermediate treatment is more convenient; expensive alkyl halide (such as methyl iodide) cannot be used as a reaction raw material, cheaper sulfolipid or phosphate ester compounds are selected, a good implementation effect is also obtained, and the product has a cost advantage.

Description

technical field [0001] The invention relates to a preparation method of arecoline, which belongs to the technical field of chemical synthesis. Background technique [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 an 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 US2506458 introduced the synthesis method of arecoline earlier, which is prepared from 3,3'-iminodipropionitrile through N-methylation, nitrilation, condensation cyclization, catalytic hydrogenation and other steps. Arecoline. This method has rare raw materials and complicated preparation process, so people no longer use it. [0004] D...

Claims

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Application Information

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IPC IPC(8): C07D211/78
CPCC07D211/78
Inventor 刘乃山李静洁刘翠珍
Owner QINGDAO KANGYUAN PHARMA
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