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Synthesis of (r,s-)nicotine

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

Active Publication Date: 2022-02-22
SHANDONG JINCHENG KERUI CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The process route used in this patent has low yield and requires more reagents in each step, and the cost is high, so it is not suitable for scale-up production
[0007] Generally speaking, the method for preparing racemic nicotine in the prior art not only uses expensive reagents, but also often adopts low-temperature (or ultra-low temperature) reaction, with many steps and long reaction cycle, and the separation and purification operation of each step is complicated, which increases the production cost , it is difficult to use in industrial production

Method used

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  • Synthesis of (r,s-)nicotine
  • Synthesis 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 flask, after nitrogen replacement, irradiated with light of 350nm wavelength, stirred at room temperature overnight; after the reaction was completed, formaldehyde solution was added to control the temperature at 30°C, formic acid was added dropwise, and the reaction was monitored 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 pharmaceutical intermediates, in particular to a method for synthesizing (R,S-)nicotine. The method comprises the following steps: (1) using methyl nicotinate and N-butenyl pyrrolidone as raw materials to prepare N-butenyl-3-benzoyl-1-pyrrolidone through condensation reaction; (2) after the reaction is finished, carry out hydrolysis Reaction, cooling, adjusting the pH to be alkaline, extracting, separating the organic phase, concentrating, and distilling to obtain the enamine intermediate; (3) the enamine intermediate uses metal oxides or complexes as The reduction catalyst carries out the reduction reaction to obtain the target product (R,S-)nicotine. The method innovatively proposes the use of a metal catalyst to prepare (R,S-)nicotine under the light of a specific wavelength. The method is easy to operate, high in yield, and low in cost, and is suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical intermediates, in particular to a method for synthesizing (R,S-)nicotine. Background technique [0002] Nicotine, commonly known as nicotine, is an alkaloid present in Solanaceae plants (Solanum genus) and is also an important component of tobacco. In addition to tobacco, nicotine also exists in the fruits of a variety of Solanaceae plants, such as tomatoes, wolfberries and other plants that contain nicotine, and these vegetables and medicinal materials are recognized as healthy foods that are beneficial to the human body. [0003] Racemic nicotine (R, S-nicotine) has essentially similar pharmacological activity to natural nicotine (S-nicotine), but its action time is slightly slower than natural nicotine, but its toxicity is much lower than natural nicotine. At present, the nicotine used in the market is mainly natural nicotine, which is mainly extracted from tobacco and other plants. The...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04B01J27/122B01J21/08
CPCC07D401/04B01J21/08B01J27/122
Inventor 刘艳春刘镇张世磊
Owner SHANDONG JINCHENG KERUI CHEMICAL CO LTD
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