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Synthesis method of (R, S-) nicotine

A synthetic method, nicotine technology, applied in chemical instruments and methods, organic chemistry, physical/chemical process catalysts, etc., can solve the problems of long reaction cycle, many steps, low yield of process route, etc., and achieve high synthesis specificity , mild reaction conditions and high product purity

Active Publication Date: 2021-05-04
SHANDONG JINCHENG KERUI CHEMICAL CO LTD
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AI Technical Summary

Benefits of technology

This patented technology allows for efficient production of reduced-nicotinic acid by reacting an alkaloid with nitrogen gas at specific wavelengages. By doing this process overcomes problems such as poor yields or harsh reactions that may be caused when starting from other compounds like nornitives. Additionally, these processes can produce highly pure products without causing discomfort during use.

Problems solved by technology

This technical problem addressed by this patented technology relates to improving the efficiency and effectiveness of producing pure or enantiomerically active compounds containing one type of nitrogen atom called nicotinc without requiring multiple chemical processes at different temperatures.

Method used

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  • Synthesis method of (R, S-) nicotine

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preparation example Construction

[0034] The synthetic method of described (R, S-) nicotine comprises the steps:

[0035] (1) In a reaction vessel, add methyl nicotinate and N-butenylpyrrolidone to prepare N-butenyl-3-benzoyl-1-pyrrolidone in a suitable solvent under alkaline conditions; after the reaction , adding a suitable aqueous solution of inorganic acid to carry out hydrolysis reaction; after cooling, adding lye to adjust the pH value to 10, extracting with a suitable organic solvent, separating the organic phase, concentrating, and distilling the mother liquor to obtain an enamine intermediate;

[0036] (2) Disperse the enamine intermediate in a suitable solvent, add a metal reduction catalyst under light, and perform a reduction reaction at a suitable temperature; perform a methylation reaction after the reaction, filter, concentrate the filtrate, and distill the bottom liquid The target product (R,S-)nicotine was obtained.

[0037] In step (1), the suitable solvent is one or more of diethyl ether, d...

Embodiment 1

[0041] Add 150g of sodium ethoxide and 1000mL of dichloromethane into the three-necked flask, install the magnet and condenser, and replace the system with nitrogen; mix 100g of methyl nicotinate and 117g of N-butenylpyrrolidone with 200mL of dichloromethane, and the system Slowly raise the temperature to 50°C, add the mixed solution dropwise, continue to keep warm for 3 hours, then cool to 5°C, add 6N (ie: 6mol / L) phosphoric acid dropwise to quench the reaction, adjust the pH value to 4 and react for 8 hours; At the end of the reaction, 6N lye was added to adjust the pH value to 10, and dichloromethane was added to extract three times; the organic phases were combined, dried, concentrated, and distilled to obtain 9.158 g of a light yellow oily enamine intermediate, with a yield of 81%.

Embodiment 2

[0043] Disperse the obtained enamine intermediate in 100 mL of methanol and add 1 g of SiO 2 / TiO 2 Catalyst (SiO 2The mass fraction is 5.5%), placed in a reaction bottle, after nitrogen replacement, irradiated with light of 350nm wavelength, stirred at room temperature overnight; after the reaction, add formaldehyde solution to control the temperature at 30°C, add formic acid dropwise, and monitor the reaction by TLC. After the completion of filtration, the filtrate was concentrated to obtain crude (R,S-)nicotine, which was distilled to obtain 8.3g of colorless and transparent pure product (68-70°C, 0.2mmHg), with a GC purity of 99.6% and a yield of 90%.

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Abstract

The invention belongs to the technical field of medical intermediates, and particularly relates to a synthesis method of (R, S-) nicotine. The method comprises the following steps: (1) taking methyl nicotinate and N-butenyl pyrrolidone as raw materials, and preparing N-butenyl-3-benzoyl-1-pyrrolidone through a condensation reaction; (2) after the reaction is finished, carrying out hydrolysis reaction, cooling, adjusting the pH value to be alkaline, extracting, separating out an organic phase, concentrating and distilling to obtain an enamine intermediate; and (3) carrying out a reduction reaction on the enamine intermediate under illumination with the wavelength of 200-400nm by using a metal oxide or a complex as a reduction catalyst to obtain the target product (R, S-) nicotine. According to the method, use of the metal catalyst is innovatively proposed, reaction is initiated by illumination with specific wavelength to prepare the (R, S-) nicotine, and the method is simple and convenient to operate, high in yield, low in cost and suitable for industrial large-scale production.

Description

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Claims

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Application Information

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Owner SHANDONG JINCHENG KERUI CHEMICAL CO LTD
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