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Preparation method of nicotine and intermediate thereof

A technology of intermediates and nicotine, which is applied in the field of preparation of nicotine and its intermediates, can solve the problems of low conversion rate of intermediates and harsh reaction conditions, and achieve the effects of high conversion rate, easy availability of raw materials and mild reaction conditions

Active Publication Date: 2021-06-01
上海零诺生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] But the reaction conditions of this reaction are very harsh, for example, the reaction containing tert-butyllithium (the second step) needs to control the temperature at -120 °C, and the intermediate low conversion rate

Method used

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  • Preparation method of nicotine and intermediate thereof
  • Preparation method of nicotine and intermediate thereof
  • Preparation method of nicotine and intermediate thereof

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preparation example Construction

[0065] The second aspect of the present invention relates to the preparation method of the above-mentioned intermediate, comprising the following steps:

[0066] S110: reacting the compound shown in formula (II-1) and the compound shown in formula (II-2) to prepare the compound shown in formula (II-3).

[0067]

[0068] R 1 As defined in the first aspect of the present invention, details are not repeated here.

[0069] The compound represented by formula (II-1) (ie, 3-pyridinecarbaldehyde) and the compound represented by formula (II-2) can be commercially available raw materials, or can be prepared by existing methods.

[0070] In one embodiment, the compound shown in formula (II-2) is tert-butylsulfinamide (i.e. R 1 for tert-butyl).

[0071] In one embodiment, step S110 includes the following steps:

[0072] S111: Mix the compound represented by the formula (II-1), the compound represented by the formula (II-2), the base and the solvent, and react at a temperature of 2...

Embodiment 1

[0143]

[0144] Take 100g of 3-pyridinecarbaldehyde, 100.5g of tert-butylsulfinamide, and 180.5g of cesium carbonate, dissolve them in 700ml of dichloromethane, stir and react at 25°C (room temperature) for 4h, and check the completion of the reaction by LC-MS. The reaction is complete Afterwards, the solid impurities were removed by filtration, and the dichloromethane solvent was recovered by distillation under reduced pressure to obtain 190.5 g of 2-methyl-N-(pyridine-3-methylene)propane-2-sulfinamide, with a yield of 97%. figure 1 .

Embodiment 2

[0146]

[0147] Take 95g of magnesium chips, disperse them with 200ml of tetrahydrofuran, and put them into the reaction flask, under nitrogen protection, dissolve 2-(2-bromoethyl)-1,3-dioxane with 300ml of tetrahydrofuran, and then put it in an ice bath ( -15°C) was added into the reaction flask in 6 batches within 1 hour, and after the exothermic end, the reaction temperature was raised to 50°C for 4 hours to initiate the Grignard reagent.

[0148] Take 190g of the product 2-methyl-N-(pyridine-3-methylene)propane-2-sulfinamide in Example 1, dissolve it in 500ml of tetrahydrofuran, and then divide it in an ice bath (-15°C) within 1h. Add to the reaction flask five times, react at 25°C (room temperature) for 5h, check the completion of the reaction by LC-MS, after the reaction is complete, quench the reaction with saturated ammonium chloride aqueous solution, filter the solid impurities, concentrate the water phase volume to 800ml, and use 1200ml of ethyl acetate was extrac...

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Abstract

The invention relates to a preparation method of nicotine and an intermediate thereof, wherein the intermediate has a structure as shown in a formula (II), X1, X2 and X3 are respectively and independently CR2R3, R1 is a C1-6 alkyl group, and R2 and R3 are each independently H or a C1-6 alkyl group. According to the invention, the preparation method of the nicotine and the intermediate thereof has the advantages of simple operation, mild reaction conditions, easily available raw materials, and high conversion rate, can effectively reduce the production cost of the nicotine, and has the potential of industrial production, and each reaction can be directly post-fed through simple post-treatment basically.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of nicotine and its intermediates. 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. In recent years, with the rapid development of the e-cigarette industry, e-cigarettes have become the first choice for people to quit smoking, and nicotine, as the core functional ingredient in e-cigarettes, can enable people who quit smoking to quickly receive nicotine supplements and reduce withdrawal reactions. [0003] The rapid growth of the electronic cigarette industry has also increased the demand for nicotine. However, most of the commercially available nicotine is extracted from tobacco. Due to factors such as the growth of tobacco raw materials, pro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/12C07D401/04
CPCC07D405/12C07D401/04
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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