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Method for preparing 5, 8-dihydro-6H-isoquinoline [3, 2-alpha] isoquinoline based on micro-reaction system

A technology of isoquinoline and micro-reaction, applied in the direction of organic chemistry, can solve the problems of low production capacity, high price and high cost

Active Publication Date: 2021-07-06
SICHUAN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, the synthesis steps are relatively cumbersome and the operation is complicated; the preparation process requires expensive transition metals and excessive acid catalysis, so the production capacity is low and the cost is high

Method used

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  • Method for preparing 5, 8-dihydro-6H-isoquinoline [3, 2-alpha] isoquinoline based on micro-reaction system
  • Method for preparing 5, 8-dihydro-6H-isoquinoline [3, 2-alpha] isoquinoline based on micro-reaction system
  • Method for preparing 5, 8-dihydro-6H-isoquinoline [3, 2-alpha] isoquinoline based on micro-reaction system

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0120] This example provides a method for preparing 5,8-dihydro-6H-isoquinoline[3,2-α]isoquinoline using a micro reaction system. like figure 1 As shown, the micro reaction system includes feed pump one 1 connected in sequence, the first micro mixer 2, feed pump two 3, the first fixed bed reactor 4, dehydrating agent and silica filler 5, the first back Pressure valve 6, hydrogen passage 7, gas mass flowmeter 8, second micro-mixer 9, second fixed-bed reactor 10, reducing agent and silica packing 11, condenser 12, nitrogen passage 13, gas-liquid separator 14, the second back pressure valve 15, feed pump three 16, the third micro-mixer 17, feed pump four 18, microchannel reactor 19 the third back pressure valve 20, the first port 21, the second port 22 and The third interface 23 .

[0121] Preparation of the first fixed bed reactor

[0122] will be 2g Molecular sieves (20-40 mesh) are dispersed in 20 g of silica (particle diameter 0.5 mm-1.0 mm), and the formed dehydrating a...

Embodiment 2

[0137] Preparation of the first fixed bed reactor

[0138] 0.2g Molecular sieves (20-40 mesh) are dispersed in 20 g of silica (particle diameter 0.5 mm-1.0 mm), and the formed dehydrating agent and silica filler 5 are filled in the first fixed-bed reactor 4 . The first fixed bed reactor 4 can be a tubular microchannel reactor, the length of the tubular microchannel reactor can be 20 cm, and the inner diameter can be 1 cm.

[0139] Preparation of the second fixed bed reactor

[0140] 0.2gPd(OH) 2 / C (10wt%) is dispersed in 20g of silica (particle diameter 0.5mm-1.0mm), and the formed reducing agent and silica filler 11 are filled in the second fixed-bed reactor 10 . The second fixed bed reactor 10 can be a tubular microchannel reactor, the length of the tubular microchannel reactor can be 20 cm, and the inner diameter can be 1 cm.

[0141] Preparation of dihydroberberine

[0142]

[0143] (1) if figure 1 As shown, two inlets of the first micro-mixer are connected with...

Embodiment 3

[0153] Preparation of the first fixed bed reactor

[0154] 7g of Molecular sieves (20-40 mesh) are dispersed in 0.7g of silica (particle size 0.5mm-1.0mm), and the formed dehydrating agent and silica filler 5 are filled in the first fixed-bed reactor 4 . The first fixed bed reactor 4 can be a tubular microchannel reactor, the length of the tubular microchannel reactor can be 20 cm, and the inner diameter can be 1 cm.

[0155] Preparation of the second fixed bed reactor

[0156] 20gPd(OH) 2 / C (10wt%) is dispersed in 2g of silica (particle diameter 0.5mm-1.0mm), and the formed reducing agent and silica filler 11 are filled in the second fixed-bed reactor 10 . The second fixed bed reactor 10 can be a tubular microchannel reactor, the length of the tubular microchannel reactor can be 20 cm, and the inner diameter can be 1 cm.

[0157] Preparation of dihydroberberine

[0158]

[0159] (1) if figure 1 As shown, two inlets of the first micro-mixer are connected with feed p...

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Abstract

The invention provides a method for preparing 5, 8-dihydro-6H-isoquinoline [3, 2-alpha] isoquinoline based on a micro-reaction system. A first solution and a second solution are introduced into a first micro-mixer through a feeding pump to be mixed; a mixture of an arylethylamine solution and an aryl aldehyde solution is pumped into a first fixed bed reactor through the first micro-mixer to be subjected to a dehydration condensation reaction; the mixture subjected to the dehydration condensation reaction is introduced into a second fixed bed reactor through a second micro-mixer for catalytic hydrogenation; the mixed material subjected to catalytic hydrogenation and a methanol solution of saturated hydrochloric acid are introduced into a micro-channel reactor through a third micro-mixer for a salt forming reaction, and vacuum concentration, pulping and purification are carried out to obtain secondary amine hydrochloride; and in the presence of acid, a dehydrating agent and an additive, the secondary amine hydrochloride and a glyoxal solution are subjected to Pictet-Spengler reaction and Friedel-Crafts hydroxyalkylation and dehydration cascade reaction, so as to obtain the 5, 8-dihydro-6H-isoquinoline [3, 2-alpha] isoquinoline compound.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for continuously preparing 5,8-dihydro-6H-isoquinoline [3,2-α]isoquinoline (I) by a micro-reaction system. [0002] Background technique [0003] 5,8-dihydro-6H-isoquinoline [3,2-α] isoquinoline (I) is a key intermediate for synthesizing berberine hydrochloride and other proberberine and tetrahydroberberine. Berberine hydrochloride (berberine, berberine) is an isoquinoline alkaloid with many pharmacological activities extracted from the rhizomes of Coptidis Rhizoma, Cortex Phellodendron and Three Needles. Berberine hydrochloride is widely used in traditional Chinese patent medicines, and has the functions of clearing away heat, detoxifying, and purging fire. It was originally used clinically and has an antibacterial effect. It is used to treat bacterial gastrointestinal inflammation and bacillary dysentery and other indications. It also shows good curativ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D455/03C07D471/04
CPCC07D455/03C07D471/04
Inventor 陈芬儿唐培李伟剑陈文昌陈煜
Owner SICHUAN UNIV
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