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Preparation method of polysubstituted bromomethyl benzo nitrogenous heterocyclic compound

An extraction and extraction device technology, applied in the field of pharmaceutical intermediate preparation, can solve the problems of inconvenient vibration operation of the extraction device, difficult implementation of the extraction process, small volume of the extraction device, etc., achieves good preparation effect, strong inventive concept and creativity, fixed strong enough effect

Active Publication Date: 2020-12-04
烟台宁远药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The first purpose of the present invention is to solve two specific problems in the prior art, one is starting from o-bromobenzylamine, how to obtain 3-methyl-8-bromomethyl isoquinol through few steps with high yield The problem of phenoline hydrobromide, this application scheme perfectly solves this problem, and the second is that it is difficult to implement the extraction link, the volume of the extraction device is too small, and the vibration operation of the extraction device is too large, which is inconvenient. Both are addressed in this application

Method used

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  • Preparation method of polysubstituted bromomethyl benzo nitrogenous heterocyclic compound
  • Preparation method of polysubstituted bromomethyl benzo nitrogenous heterocyclic compound
  • Preparation method of polysubstituted bromomethyl benzo nitrogenous heterocyclic compound

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Embodiment 1

[0053] An ultrasonic extraction device is characterized by comprising an extraction part 1, a shell part 2, an ultrasonic part 3, a cross bar part 4, a left support part 5, a right support part 6, a glassware 7 and a demulsification component 8. The extraction device can be divided into multiple specifications, for example, the volume of the extraction part can be 1L, 2L, 3L, 4L, 5L to meet different requirements.

[0054] The extraction part 1 comprises a cylindrical part 11, an upper opening 12, an upper cover 13, a cone part 14, a liquid stopper group 15 and a liquid outlet 16. The main part of the extraction part 1 is spliced from top to bottom by an upper opening 12, a cylindrical part 11 and a conical part 14, the cylindrical part 11 is hollow, the upper opening 12 is larger and smaller, and the inner side is a frosted part 121; the outer edge of the upper cover 13 adapted to the frosted part 121 is a frosted surface; the upper center of the upper cover 13 is provided with a...

Embodiment 2

[0063] A preparation method of polysubstituted bromomethylbenzo nitrogen-containing heterocyclic compounds, which requires a large amount of extraction dose, is carried out by using an ultrasonic extraction device as described above, and is characterized by comprising the following steps.

[0064] (1) dissolve 64-68g acetone acetal in 1900-2100ml toluene, add 105-115g o-bromobenzylamine while stirring, raise the temperature to about 120℃, react until water division is finished, confirm that the reaction is complete through LCMS detection, and concentrate to obtain pale yellow liquid N-(2- bromophenyl)-1,1-dimethoxypropyl -2-.

[0065] (2) 165-175g of N-(2- bromophenyl)-1,1-dimethoxypropane -2- imine is dissolved in 1600-300ml of ethanol, the temperature is controlled to below 30-35 degrees Celsius, 55-59g of sodium borohydride is slowly added in batches, and after the addition is finished, the reaction is continued at 30-35 degrees Celsius for 8 hours. Add at least 1L of water to ...

Embodiment 3

[0071] A preparation method of polysubstituted bromomethylbenzo nitrogen-containing heterocyclic compounds, which requires a large amount of extraction dose, is carried out by using an ultrasonic extraction device as described above, and is characterized by comprising the following steps.

[0072] (1) 68g acetone acetal was dissolved in 2100ml toluene, 113.33g o-bromobenzylamine was added under stirring, the temperature was raised to about 120℃, and the reaction was completed. LCMS detection confirmed that the reaction was complete, and the light yellow liquid N-(2- bromophenyl)-1,1-dimethoxypropyl -2- imine was obtained by concentration. The yield is 100%.

[0073] (2) Dissolve 175g of N-(2- bromophenyl)-1,1-dimethoxypropyl -2- imine in 1800ml of ethanol, control the temperature to below 32℃, slowly add 59g of sodium borohydride in batches, keep the reaction at 32℃ for 10h after the addition, and confirm the reaction is complete by LCMS detection. Drop 300ml of water and concentr...

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Abstract

The invention relates to a preparation method of a polysubstituted bromomethyl benzo nitrogenous heterocyclic compound. The preparation method is carried out by using an ultrasonic extraction device,and is characterized by comprising the following steps: reacting pyruvic aldehyde dimethyl acetal with o-bromobenzylamine in toluene to obtain N-(2-bromophenyl)-1,1-dimethoxypropan-2-imine; and carrying out five steps to obtain 3-methyl-8-bromomethyl isoquinoline hydrobromide which is a final product. Extraction is implemented by an ultrasonic extraction device, and a preparation step, a coveringstep, a vibration shaking step, a repeating step and a receiving step are included. The ultrasonic extraction device comprises an extraction part (1), a shell part (2), an ultrasonic part (3), a transverse rod part (4), a left supporting part (5), a right supporting part (6), a glass device (7) and a demulsification assembly (8).

Description

Technical field [0001] The invention relates to the technical field of preparation of pharmaceutical intermediates, in particular to a preparation method of polysubstituted bromomethyl benzo nitrogen-containing heterocyclic compounds. technical background [0002] Isoquinoline and its derivatives are important compounds with strong biological activity, which are widely used in medicine, pesticide and other fields. Therefore, the synthesis of pyrazole derivatives has attracted wide attention, especially in pharmaceutical intermediates. A preparation method of 8- nitro -1,2,3,4- tetrahydroisoquinoline is given in CN2016100987718, a synthesis method of 4- hydroxy -8- bromoisoquinoline is given in CN201610042580.X, and a preparation method of 7- bromoisoquinoline is given in CN201210340505.3 Due to the characteristics of this molecule, unique synthetic route and unique high yield, this method can't be extended to the synthesis of other similar structures. [0003] Due to the characte...

Claims

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Application Information

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IPC IPC(8): C07D217/04B01D11/04B01J19/10
CPCC07D217/04B01D11/0423
Inventor 马强
Owner 烟台宁远药业有限公司
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