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Racemic 6-methyl nicotine as well as preparation method and application thereof

A technology of methyl nicotine and methyl nicotinic acid, applied in the application, tobacco, tobacco processing and other directions, can solve the problems of unstable production and supply, influence, poor sensory experience, etc.

Pending Publication Date: 2022-05-06
上海零诺生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the commercially available nicotine is mainly natural L-nicotine extracted from tobacco, which is affected by various factors such as the growth of tobacco raw materials, production, climate, etc., the production supply is unstable, and it is easily affected by tobacco-related policies, which is not conducive to wide application
However, in the preparation method of artificially synthesized nicotine, racemic nicotine contains nicotine in two configurations R and S. When used in new tobacco products, there is no obvious sense of satisfaction and throat hit, so chiral resolution is required, resulting in high cost
[0004] For this reason, researchers in the new tobacco industry try to develop alkaloids to replace nicotine. Traditional alkaloids can be cytisine and arecoline, etc. However, when these alkaloids are used in new tobacco products, there is no sense of satisfaction and satisfaction at all. Throat hit, poor sensory experience

Method used

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  • Racemic 6-methyl nicotine as well as preparation method and application thereof
  • Racemic 6-methyl nicotine as well as preparation method and application thereof
  • Racemic 6-methyl nicotine as well as preparation method and application thereof

Examples

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preparation example Construction

[0037] See figure 1 , the preparation method of the racemic 6-methylnicotine of one embodiment of the present invention, comprises the following steps:

[0038] S10. Mix 6-methylnicotinic acid and an alcoholic solvent, adjust the pH to ≤1, maintain the reaction temperature at 80° C. to 100° C., and obtain 6-methylnicotinic acid ester after sufficient reaction.

[0039] The preparation process of 6-methylnicotinate in step S10 is as follows:

[0040]

[0041] As shown in the above reaction equation, in step S10, 6-methylnicotinic acid and an alcoholic solvent undergo an esterification reaction under acidic conditions to generate 6-methylnicotinic acid ester.

[0042] Wherein, in the operation of maintaining the reaction temperature at 80° C. to 100° C. for sufficient reaction, 6-methylnicotinic acid and alcohol solvents can be heated to reflux under acidic conditions, and the heating and reflux time is determined according to the actual situation.

[0043] In one embodimen...

Embodiment 1

[0096] (1) The preparation process of 6-methylnicotinate is as follows:

[0097]

[0098] Add 400g of 6-methylnicotinic acid into a 5L reaction flask, then add 2L of absolute ethanol, then add 400g of thionyl chloride, and then add 1ml of DMF (dimethylformamide), reflux at 95°C for 4h, pass LC-MS monitors the completion of the reaction. After the reaction is completed, stop heating, cool down, recover the excess solvent and thionyl chloride under reduced pressure, then add sodium bicarbonate solution to adjust the pH to 8, add twice the volume of dichloromethane to extract twice , and then recover the solvent under reduced pressure to obtain ethyl 6-methylnicotinate with a yield of 90%.

[0099] (2) The preparation process of 1-methyl-3-(6-methyl-nicotinoyl)-2-pyrrolidone salt is as follows:

[0100]

[0101] Take 360g of ethyl 6-methylnicotinate obtained from the above reaction, 300g of sodium tert-butoxide and 300g of N-methylpyrrolidone, dissolve them in 2.5L of tolu...

Embodiment 2～ Embodiment 7

[0110] The preparation method of the electronic smog liquid in Examples 2 to 7 is as follows:

[0111] Take 2ml of propylene glycol and 2ml of glycerol (volume ratio: 5:5) and mix them evenly as a solvent, add 10mg, 20mg, 30mg, 50mg, 70mg, 90mg of the racemic 6-methylnicotine prepared in Example 1, Get different concentrations of racemic 6-methylnicotine solutions; then continue to take a mixed solvent of propylene glycol and glycerol (volume ratio of 5:5) to replenish the volume of different concentrations of racemic 6-methylnicotine solutions Make up to 10ml, and mix evenly on the shaker to obtain electronic cigarettes with racemic 6-methylnicotine concentrations of 1mg / ml, 2mg / ml, 3mg / ml, 5mg / ml, 7mg / ml, and 9mg / ml respectively. Liquids are the electronic cigarette liquids of Embodiment 2 to Embodiment 7 in sequence.

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Abstract

The invention relates to racemic 6-methyl nicotine as well as a preparation method and application thereof. The preparation method of racemic 6-methyl nicotine comprises the following steps: uniformly mixing 6-methyl nicotinic acid and an alcohol solvent, adjusting the pH value to be less than or equal to 1, maintaining the reaction temperature to be 80-100 DEG C, and fully reacting to obtain 6-methyl nicotinate; the method comprises the following steps: uniformly mixing 6-methyl nicotinate with N-methyl pyrrolidone, inorganic alkali and an organic solvent, maintaining the reaction temperature at 100-130 DEG C, carrying out solid-liquid separation after full reaction, and retaining a solid which is 1-methyl-3-(6-methyl-nicotinoyl)-2-pyrrolidone salt; the preparation method comprises the following steps: uniformly mixing 1-methyl-3-(6-methyl-nicotinoyl)-2-pyrrolidone salt with an acidic solvent, adjusting the pH value to be less than or equal to 1, maintaining the reaction temperature to be 100-150 DEG C, fully reacting, cooling, adjusting the pH value to be greater than or equal to 9, adding a reducing agent, uniformly mixing, maintaining the reaction temperature to be 40-80 DEG C, fully reacting, performing solid-liquid separation, and retaining liquid, thereby obtaining the 1-methyl-3-(6-methyl-nicotinoyl)-2-pyrrolidone. And separating to obtain the racemic 6-methyl nicotine.

Description

technical field [0001] The invention relates to the technical field of novel tobacco products, in particular to a racemic 6-methylnicotine, a preparation method thereof, and an application thereof. Background technique [0002] As early as the 1990s, the World Health Organization vigorously promoted "nicotine replacement therapy" for smoking cessation worldwide, helping people get rid of their physical and psychological dependence on burning cigarettes. Later, with the development of the new tobacco industry, new tobacco products such as atomized electronic cigarettes and heat-not-burn products have become the first choice for most people to quit burning cigarettes. Among them, the atomized electronic cigarettes currently on the market are formulated with propylene glycol, glycerin, flavors, nicotine, and nicotine salts; heat-not-burn products use non-tobacco herbal particles (powder) as carriers, and the required Added common additives such as nicotine, essence, sweetener ...

Claims

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Application Information

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IPC IPC(8): C07D401/04A24B15/167
CPCC07D401/04A24B15/167Y02A50/30
Inventor 潘学连董磊沈兆元
Owner 上海零诺生物科技有限公司
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