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

Preparation method of ephedrone compound

A technology for cannabinoids and compounds, applied in the field of chemical synthesis, can solve the problems of flavonoids having no psychoactive properties, being difficult to amplify, and having long synthesis steps, and achieving the effects of low synthesis cost, short production period and easy operation.

Pending Publication Date: 2022-05-13
DEYI PHARMA LTD
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Of the more than 200 bioactive compounds in cannabis, cannabinoids and terpenes have received the most attention, but cannabis also produces another important compound—cannabinoids, which make up about 10 percent of these known compounds, of which About 20 flavonoids are known to be present in cannabis, these flavonoids are not psychoactive
[0010] The disclosed chemical synthesis methods have the disadvantages of long synthesis steps, multi-step reactions requiring purification by silica gel column chromatography, and difficulty in scaling up.

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 ephedrone compound
  • Preparation method of ephedrone compound
  • Preparation method of ephedrone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1、4

[0117] The synthesis of embodiment 1,4'-hydroxyl-3'-methoxybenzoyl ethyl acetate

[0118]

[0119] Add 60% NaH (6.00 g, 150 mmol) to the reaction flask, under nitrogen protection, add toluene (60 mL) and DEC (11.82 g, 100 mmol), stir, and heat to reflux. A solution of 4'-hydroxy-3'-methoxyacetophenone (12.82 g, 50 mmol) in toluene (60 mL) was added dropwise. Reflux for 4 hours after addition. Cool down to room temperature, adjust the pH to neutral with acetic acid, add saturated ammonium chloride aqueous solution (150mL), extract the aqueous phase with ethyl acetate (100mL×3), combine the organic phases with saturated ammonium chloride aqueous solution (100mL×2 ), washed with saturated brine (100mL×2). The organic phase was dried over anhydrous sodium sulfate, filtered with suction, and the filtrate was concentrated to dryness, then added with n-hexane (50 mL) and stirred overnight. Filtration gave ethyl 4'-hydroxy-3'-methoxybenzoylacetate (15.43 g, 93.9%) as an orange-y...

Embodiment 2

[0120] Embodiment 2, the synthesis of 2-isopentenyl-1,3,5-trihydroxybenzene

[0121]

[0122] Add water (80 mL) and potassium hydroxide (4.87 g, 73.92 mmol) into the reaction flask, and stir. 1,3,5-Trihydroxybenzene (10.0 g, 79.20 mmol) was added. Cool down in an ice-water bath, add bromoisoamyl (6.6 g, 41.2 mmol) dropwise, and stir overnight. Ethyl acetate (100 mL) was added, and the pH was adjusted to 5.0 with 1N hydrochloric acid. The aqueous phase was extracted with ethyl acetate (50 mL×3), the organic phases were combined, washed with saturated brine 100 mL×2, and dried over anhydrous sodium sulfate. Suction filtration, the filtrate was concentrated to dryness, the resulting oil was separated by column chromatography (silica gel 200-300 mesh, PE:EA=8:1→2:1), and the orange oil 2-prenyl-1,3 , Synthesis of 5-trihydroxybenzene (3.17 g, 20.6%).

Embodiment 3

[0123] Embodiment 3, the synthesis of cannabinoid B and / or cannabinoid B isomer

[0124]

[0125] Add 4'-hydroxy-3'-methoxybenzoyl ethyl acetate (18.0g, 75.6mmol) and 2-isopentenyl-1,3,5-trihydroxybenzene (9.8g, 50.5 mmol), stir. Under nitrogen protection, heat to 200°C and maintain the temperature for 3 hours. Down to room temperature, the resulting product was subjected to repeated normal-phase silica gel column chromatography (silica gel 200-300 mesh, PE:EA=10:1→2:1) and then repeated reverse-phase silica gel column chromatography (reversed-phase silica gel 200 -300 mesh, water:methanol=80:20→30:70), and recrystallized by methanol to obtain about 1g of orange-yellow solid cannabinoid B (yield about 5.4%), and simultaneously obtain orange-yellow solid cannabinoid B isomer About 1g (yield about 5.4%).

[0126] Cannabinoid B: MS (ESI): 369.1 [M+H] + , 1 H NMR (400MHz, DMSO-d 6 ),δ:13.22(s,1H),10.83(s,1H),9.95(s,1H),7.56(d,1H,),7.54(s,1H),6.92(d,1H),6.89(s ,1H), 6.55(...

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 discloses a preparation method of a large ephedra ketone compound. The preparation method has the advantages of cheap and easily available raw materials, few reaction steps, short production period, simplicity and convenience in operation and the like. The method comprises the following steps: condensing 4 '-hydroxy-3'-methoxyacetophenone and diethyl carbonate (DEC) under an alkaline condition to obtain 4 '-hydroxy-3'-methoxybenzoyl ethyl acetate; the preparation method comprises the following steps: reacting 1, 3, 5-trihydroxybenzene with bromo-isoamylene under the alkaline condition to obtain 1, 3, 5-trihydroxybenzene, and reacting 1, 3, 5-trihydroxybenzene with bromo-isoamylene under the alkaline condition to obtain 2-isopentenyl-1, 3, 5- And finally, condensing the 4 '-hydroxy-3'-methoxybenzoylacetate and the 2-isopentenyl-1, 3, 5-trihydroxy benzene at high temperature to generate the ephedrone B and / or the ephedrone B isomer, and then separating and purifying to obtain the ephedrone B pure product and the ephedrone B isomer pure product.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a preparation method of cannabinoids, in particular to a preparation method of cannaflavone B and cannabinoid B isomers. Background technique [0002] Of the more than 200 bioactive compounds in cannabis, cannabinoids and terpenes have received the most attention, but cannabis also produces another important compound—cannabinoids, which make up about 10 percent of these known compounds, of which About 20 flavonoids are known to be present in cannabis, and these flavonoids are not psychoactive. [0003] Cannabis flavonoid B (Cannflavin B) has been confirmed by research as early as 1985 to have anti-inflammatory effect, and the anti-inflammatory effect is nearly 30 times higher than that of acetylsalicylic acid (sold in the form of aspirin). Compared with other painkillers, this ingredient does not make patients dependent on the drug and the risk of addiction occurs. ...

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): C07D311/30C07D311/40C07C67/00C07C69/738C07C37/18C07C39/06
CPCC07D311/30C07D311/40C07C67/00C07C37/18C07C69/738C07C39/06C07C67/343
Inventor 罗军禄牟洪涛杜业松谭昕王曙宾张平平蓝蓝
Owner DEYI PHARMA LTD
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