Unlock instant, AI-driven research and patent intelligence for your innovation.

Method for preparing 2-benzyl-3,4-dihydro-2H-isoquinoline-1-ketone derivative

A technology of isoquinoline and derivatives, applied in the preparation of 2-benzyl-3,4-dihydro-2H-isoquinolin-1-one derivatives, the field of isoquinolin-1-one derivatives, It can solve the problems of complex process and low yield, and achieve the effects of simple reaction conditions, cumbersome solution process and improved reaction efficiency.

Inactive Publication Date: 2018-05-15
SHANGHAI INST OF TECH
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Aiming at the above-mentioned technical problems in the prior art, the present invention provides a preparation method of 2-benzyl-3,4-dihydro-2H-isoquinolin-1-one derivatives, the 2- The preparation method of benzyl-3,4-dihydro-2H-isoquinolin-1-one derivatives should solve the problem of preparing 2-benzyl-3,4-dihydro-2H-isoquinolin-1 in the prior art -Technical problems of complex process and low yield in the method of ketone derivatives

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
  • Method for preparing 2-benzyl-3,4-dihydro-2H-isoquinoline-1-ketone derivative
  • Method for preparing 2-benzyl-3,4-dihydro-2H-isoquinoline-1-ketone derivative
  • Method for preparing 2-benzyl-3,4-dihydro-2H-isoquinoline-1-ketone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] A method for preparing 2-benzyl-3,4-dihydro-2H-isoquinolin-1-one derivatives, the preparation process specifically comprising the following steps: °C

[0025] CuCl 2 (16mg), glacial acetic acid (12ul), activated molecular sieve ( 200mg) into a 25ml round bottom flask at one time. The solvent toluene (5ml) was added, followed by tetrahydroisoquinoline (202mg, 1.52mmol), 2-bromo-4-chlorobenzaldehyde (334mg, 1.52mmol), benzyl azide (144mg, 1.08mmol), Then the reaction temperature was controlled to 100°C for 3h. The monitoring of the reaction process uses TLC petroleum ether: ethyl acetate 5:1. After the reaction, the obtained reaction solution is controlled at a pressure of 0.02Mpa and subjected to pressure filtration for 3 minutes. The obtained filtrate is first controlled at a temperature of 42°C and concentrated for 3 minutes. The concentrated solution was controlled by a rotary evaporator at a temperature of 38°C for 5 minutes, and then separated by column chromato...

Embodiment 2

[0032] A method for preparing 2-benzyl-3,4-dihydro-2H-isoquinolin-1-one derivatives, the preparation process specifically comprising the following steps:

[0033] CuCl 2 (16mg), glacial acetic acid (12ul), activated molecular sieve ( 200mg) into a 25ml round bottom flask at one time. Add solvent toluene (5ml), then add tetrahydroisoquinoline (202mg, 1.52mmol), benzaldehyde (161mg, 1.52mmol), benzyl azide (144mg, 1.08mmol), then control the reaction temperature to 100 ℃ reaction 3h. The monitoring of the reaction process used TLC petroleum ether: ethyl acetate 5; The concentrated solution was controlled by a rotary evaporator at a temperature of 38°C for 5 minutes, and then separated by column chromatography under the condition that the volume ratio of the eluent petroleum ether / ethyl acetate was 10:1 until the final product 2- Benzyl-3,4-dihydro-2H-isoquinolin-1-one derivatives, the final product is predicted to be specifically 2-benzyl-3,4-dihydro-2H-isoquinolin-1-one, p...

Embodiment 3

[0039] A method for preparing 2-benzyl-3,4-dihydro-2H-isoquinolin-1-one derivatives, the preparation process specifically comprising the following steps:

[0040] CuCl 2 (16mg), glacial acetic acid (12ul), activated molecular sieve ( 200mg) into a 25ml round bottom flask at one time. Add solvent toluene (5ml), followed by tetrahydroisoquinoline (202mg, 1.52mmol), 3-chlorobenzaldehyde (214mg, 1.52mmol), benzyl azide (144mg, 1.08mmol), then the reaction temperature Controlled to 100 ℃ reaction 3h. The monitoring of the reaction process uses TLC petroleum ether: ethyl acetate 5:1. After the reaction, the obtained reaction solution is controlled at a pressure of 0.02Mpa and subjected to pressure filtration for 3 minutes. The obtained filtrate is first controlled at a temperature of 42°C and concentrated for 3 minutes. The concentrated solution was controlled by a rotary evaporator at a temperature of 38°C for 5 minutes, and then separated by column chromatography under the con...

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 provides a method for preparing a 2-benzyl-3,4-dihydro-2H-isoquinoline-1-ketone derivative. The method comprises the following steps: by taking R1 substituted benzaldehyde, benzyl azideand tetrahydroisoquinoline as raw materials, putting a molecular sieve into a metal copper catalyst in an organic solvent, performing a reaction for 2-5 hours in the presence of additives, performingpressurized filtration on the obtained reaction liquid for 3-5 minutes at the pressure of 0.02-0.04MPa, concentrating the obtained filtrate, performing rotary evaluation on the obtained concentrate, and performing column chromatography separation with an eluant, thereby obtaining a separated product, namely the 2-benzyl-3,4-dihydro-2H-isoquinoline-1-ketone derivative. The 2-benzyl-3,4-dihydro-2H-isoquinoline-1-ketone derivative is prepared by using a 'one-pot method', the yield of the product can be up to 75% at most, meanwhile the reaction efficiency is greatly improved, and the method is simple in aftertreatment and relatively good in industrial application prospect.

Description

technical field [0001] The invention belongs to the field of organic chemistry and relates to an isoquinolin-1-one derivative, specifically a 2-benzyl-3,4-dihydro-2H-isoquinolin-1-one derivative Preparation. Background technique [0002] 2-benzyl-3,4-dihydro-2H-isoquinolin-1-one derivatives belong to natural heterocyclic compounds, have very important physiological and biological activities, and are very important biologically active drugs. Therefore, it is very important for researchers to study its more effective preparation method. At present, the reports on isoquinoline functionalized substances all adopt a multi-step method. After the reaction of isoquinoline with or without a protecting group is used to obtain the corresponding product, the protecting group is removed to obtain a reaction intermediate, and then combined with Benzaldehyde reacts to give the final product. This method needs at least three steps of reaction, the process is loaded down with trivial deta...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07D217/24
CPCC07D217/24
Inventor 易封萍付超苏举超黄颖孙启辉易维银
Owner SHANGHAI INST OF TECH