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Imine salt derivative, preparation method thereof and preparation method of nicotine

A technology of imide salts and derivatives is applied in the field of preparation of organic synthesis, can solve the problems of incomplete reaction of intermediate pyrrolidinol, unsuitable for industrial large-scale production, expensive starting materials, etc., and achieves high synthesis rate and synthetic Mild process conditions and high purity results

Inactive Publication Date: 2019-12-31
SHENZHEN HELGETECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The starting materials of this method are very expensive, and the intermediate pyrrolidinol reduction step has the problems of incomplete reaction and low conversion rate, and is not suitable for large-scale industrial production

Method used

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  • Imine salt derivative, preparation method thereof and preparation method of nicotine
  • Imine salt derivative, preparation method thereof and preparation method of nicotine
  • Imine salt derivative, preparation method thereof and preparation method of nicotine

Examples

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preparation example Construction

[0048] Such as figure 1 Shown, above-mentioned iminium salt derivative, its preparation method process step is as follows:

[0049] a. Add nicotinic acid, toluene and catalyst into the reactor in turn, and react under stirring and heating conditions to obtain a mixed solution; the mixed solution is concentrated under reduced pressure to remove the solvent to obtain a white solid; Down stirring, continue reaction.

[0050] In this step, the molar ratio of nicotinic acid to the catalyst is 1:5, and the catalyst is thionyl chloride or oxalyl chloride, preferably thionyl chloride; toluene is used as a solvent to dissolve nicotinic acid and the catalyst, which is beneficial to the reaction . Since nicotinic acid and the catalyst are insoluble in toluene at room temperature, they need to be heated to 50-80° C. (preferably 70° C.) during the dissolution process and stirred while heating. During the reaction process, in order to ensure constant temperature heating, the oil temperat...

Embodiment 1

[0090] Synthesis of imide derivatives, i.e. intermediate hydrochloride compounds

[0091]

[0092] Add 1.0g (8.1mmoL, 1eq) of nicotinic acid, 3mL of toluene, and 3mL of thionyl chloride (41.3mmoL, 5eq) in sequence, stir at room temperature to insoluble, heat the oil at 70°C for 0.5h to dissolve, and obtain a colorless transparent solution; After heating and reacting for 3 h, TLC showed that the raw material was completely reacted. Concentrate the above reaction solution under reduced pressure at 60°C to obtain a white solid, add 6mL of methanol, stir at room temperature (30°C) for 0.5h, adjust the pH to 9 with 5% aqueous sodium carbonate (the test paper shows dark green), and add 30mL of acetic acid Extracted twice with ethyl ester and concentrated under reduced pressure to obtain 0.67 g of methyl nicotinate.

[0093] Add NaH (2.4g) into 20mL toluene, stir at room temperature (25°C) for 10min, add N-methylpyrrolidone (3.65g) and stir at room temperature (25°C) for 15min, n...

Embodiment 2

[0097] The difference with Example 1 is: the first quenching agent is selected potassium hydroxide aqueous solution; Alcohol extractant is selected ethyl acetate; The alkaline reagent that condensation reaction adopts is sodium ethylate; Sulfuric acid was used in the example.

[0098] Add concentrated sulfuric acid to 1-methyl-3-nicotinoyl-2-pyrrolidone (2.0g) aqueous solution, exotherm, the reaction solution is light yellow, reflux at 110°C for 24h, cool down to 10°C, and distill off water under reduced pressure , adding acetone to recrystallize to obtain the sulfate salt of the intermediate (1.6g).

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Abstract

The invention discloses an imine salt derivative, a preparation method thereof and a preparation method of nicotine. The preparation method of nicotine includes the steps of: adding an imine salt derivative shown as general formula (I) or (II) in the specification and a reducing agent into a solvent for reaction to prepare a racemic nicotine solution; adding a second quenching agent into the racemic nicotine solution to obtain a nicotine precursor solution; and adding an extracting agent into the nicotine precursor solution, conducting reduced pressure concentration, and performing drying andremoving the solvent, thus obtaining nicotine. According to the invention, through the imine salt derivative intermediate synthesized for the first time and the use of the cheap reducing agent, the intermediate is reduced under a relatively mild condition to obtain racemic nicotine. Compared with the existing nicotine synthesis process, the method has the advantages of mild synthesis process conditions, simple equipment requirement, high product purity and high synthesis rate, and is particularly suitable for industrial production.

Description

technical field [0001] The invention relates to the field of preparation of organic synthesis, in particular to an imide salt derivative, a preparation method thereof and a preparation method of nicotine. Background technique [0002] Nicotine (Nicotine), commonly known as nicotine, is an alkaloid present in Solanaceae plants (Solanum genus), an important component of tobacco, and a typical nicotinic acetylcholine receptor agonist. The central nervous system has a regulatory effect. [0003] Nicotine can be addictive or dependent, and repeated use of nicotine also increases heart rate and blood pressure and reduces appetite. Large doses of nicotine can cause vomiting and nausea, and in severe cases, people can die. At the same time, nicotine and its derivatives are effective drugs for the treatment of Parkinson's syndrome, Alzheimer's disease, schizophrenia, epilepsy and depression. [0004] In recent years, with the rapid development of the electronic cigarette industry,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C07C51/41C07C63/08C07C303/32C07C309/19C07F9/38
CPCC07C51/412C07C303/32C07D401/04C07F9/3834C07C2602/42C07C63/08C07C309/19
Inventor 欧军韩魁元
Owner SHENZHEN HELGETECH CO LTD
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