Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method of artificially synthesized raceme nicotine

A technology of artificial synthesis and racemate, applied in the direction of organic chemistry, can solve the problems of many steps, increased cost, and inability to scale production, etc., and achieve the effect of mild reaction conditions, simple process, and low cost

Inactive Publication Date: 2017-08-04
FEELLIFE BIOSCI INT
View PDF2 Cites 11 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] Using butyllithium to exchange metals on 3-bromopyridine at low temperature also has the disadvantage of not being able to produce on a large scale
[0020] In a word, the existing methods for preparing racemic nicotine not only use expensive reagents, but also often adopt low-temperature reactions, many steps and long reaction cycles, which increase the cost and are difficult to be used in industrial production.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of artificially synthesized raceme nicotine
  • Preparation method of artificially synthesized raceme nicotine
  • Preparation method of artificially synthesized raceme nicotine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: the synthesis of racemate nicotine

[0035] 4-Methylamino-1-(3-pyridine)-butanone hydrochloride (13.8g, 0.055mol), dissolved in 160mL water, adjusted with 5mol / L potassium hydroxide or sodium hydroxide at -5°C Weakly alkaline to pH 8, stirred and reacted for 5 hours, concentrated, and the concentrate was refined with a mixture of water and methanol to obtain an intermediate. The intermediate was dissolved in a mixture of 180mL (how much) water and ethanol, and sodium borohydride (3.8g) was added at -5°C, heated to 15°C and stirred for 2 hours, extracted with ethyl acetate, dried and concentrated to give a light yellow oil Add 110mL of water to the crude product, distill it off directly, extract the water with 270mL of n-hexane or tetrahydrofuran, dry and concentrate to obtain 7.9g of oil, with a yield of 72%. HPLC purity 99.2%. (In the following examples, the amount of the above red words must be supplemented)

Embodiment 2

[0036] Embodiment 2: the synthesis of racemate nicotine

[0037] 4-Methylamino-1-(3-pyridine)-butanone hydrochloride (25.1g, 0.1mol), dissolved in 150mL of water and methanol, adjusted to pH 8.5 with sodium carbonate or potassium carbonate at 0°C, stirred for reaction After 3 hours, concentrate and refine the concentrate with a mixture of water and chloroform to obtain an intermediate. The intermediate was dissolved in 160mL of methanol, and lithium tetrahydrohydride (3.7g, 0.1mol) was added at 0°C, heated to 25°C, stirred and reacted for 2 hours, extracted with dichloromethane, dried and concentrated to obtain a crude light yellow oil, added water 210mL, directly distilled out, water was extracted with 290mL petroleum ether or diethyl ether, dried and concentrated to obtain 12.5g of oil. HPLC purity 99.5%.

Embodiment 3

[0038] Embodiment 3: the synthesis of racemate nicotine

[0039] 4-Methylamino-1-(3-pyridine)-butanone hydrochloride (25.1g, 0.1mol), dissolved in 165 mL of water and ethanol, adjusted to pH 7.5 with sodium bicarbonate or potassium bicarbonate at 5°C, stirred After reacting for 2 hours, concentrate and refine the concentrate with a mixture of water and dichloromethane to obtain an intermediate. Dissolve the intermediate in 180mL of propanol or isopropanol, add aluminum trichloride (13.3g, 0.1mol) at 5°C, raise the temperature to 25°C, stir for 2 hours, add 200mL of distilled water, steam distillation, distilled The aqueous phase was extracted with 350 mL of ethyl acetate, and the ethyl acetate was concentrated to dryness to obtain 12.0 g of light yellow oil. HPLC purity was 99.5%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a preparation method of artificially synthesized raceme nicotine, in particular to a preparation method of obtaining the raceme nicotine through two-step reaction of 4- methylamino-1-(3-pyridine)-butanone hydrochloride. The preparation method comprises the following specific synthesis steps: (1) dissolving 4-methylamino-1-(3-pyridine)-butanone hydrochloride by using an appropriate solvent in an appropriate reaction vessel, reacting under the conditions of an alkaline solution with appropriate concentration and an appropriate temperature, concentrating after ending reaction, and then purifying by using an appropriate solvent to obtain 1-methyl-2-(3-pyridine)-2-pyrrolidinol; and (2) reacting 1-methyl-2-(3-pyridine)-2-pyrrolidinol in an appropriate solvent in the reaction vessel under the conditions of an appropriate amount of reducing agent and an appropriate temperature, concentrating after ending reaction, and then purifying by using an appropriate solvent to obtain the raceme nicotine with high content and high purity. The preparation method of the artificially synthesized raceme nicotine is simple in process, low in cost, easy to operate, mild in reaction conditions, environmentally-friendly and suitable for industrialized production.

Description

technical field [0001] The present invention relates to a kind of preparation method of synthetic racemic nicotine, specifically a kind of preparation method of racemic nicotine from 4-methylamino-1-(3-pyridine)-butanone hydrochloride through two-step reaction method. Background technique [0002] Nicotine, also known as nicotine, is an alkaloid present in Solanaceae plants and an important component of tobacco. Nicotine is a typical agonist of nicotinic acetylcholine receptors, which have important regulatory effects on the central nervous system. Studies have shown that nicotine has the potential to become an effective drug in the treatment of Parkinson's disease, Alzheimer's disease, schizophrenia, epilepsy and depression. At present, the nicotine used in the market is mainly extracted from plants such as tobacco, which is affected by many factors such as raw materials, climate, and cycle. Moreover, when nicotine is extracted from plants such as tobacco, other impuritie...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 华健吕泉福
Owner FEELLIFE BIOSCI INT
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com