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A novel compound 6,7-dibromo-1,2,3,4-tetrahydroisoquinoline and its preparation method

A technology of tetrahydroisoquinoline and compound, which is applied in the field of novel compound 6,7-dibromo-1,2,3,4-tetrahydroisoquinoline and its preparation, can solve the problem of expensive raw materials, long steps, and high cost. problems such as low rate, to achieve the effect of easy processing and purification, mild reaction

Inactive Publication Date: 2018-09-28
ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthesis of tetrahydroisoquinolines is mostly achieved through ring closure of phenethylamine molecules. The steps are long, the raw materials are expensive, difficult to operate and the yield is not high, which greatly limits the use of halogenated tetrahydroisoquinolines. Efficient preparation and application requirements of quinoline

Method used

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  • A novel compound 6,7-dibromo-1,2,3,4-tetrahydroisoquinoline and its preparation method

Examples

Experimental program
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Effect test

Embodiment 1

[0019] The preparation method of 6,7-dibromo-1,2,3,4-tetrahydroisoquinoline of the present embodiment is as follows:

[0020] (1) Synthesis of N-acetyl 1,2,3,4-tetrahydroisoquinoline

[0021] Take a 100ml single-necked bottle and put it in an ice bath, add 2.66g (0.02mol) of 1,2,3,4-tetrahydroisoquinoline, and add 100mL of dichloromethane, stir to dissolve, and then add 3.03g of triethylamine (0.03mol), after stirring evenly, weigh 2.04g (0.026mol) of acetyl chloride and slowly add it dropwise to the reaction system. Add an appropriate amount of water and dichloromethane to extract 3 times, wash the dichloromethane layer with water 1-2 times, and extract the same washed water layer with dichloromethane 1 time, combine the organic layers, dry the extract with anhydrous sodium sulfate, The solvent was removed by a rotary evaporator, and the residue was purified by column chromatography, eluting with petroleum ether / ethyl acetate=1 / 1 to obtain 3.36 g of a light yellow oil, with ...

Embodiment 2

[0040] The preparation method of 6,7-dibromo-1,2,3,4-tetrahydroisoquinoline of the present embodiment is as follows:

[0041] (1) Synthesis of N-acetyl 1,2,3,4-tetrahydroisoquinoline

[0042] Take a 100ml single-necked bottle, add 2.66g (0.02mol) of 1,2,3,4-tetrahydroisoquinoline, and add 100mL of dichloromethane, stir to dissolve, and then add 2.82g (0.028mol) of triethylamine , after stirring evenly, weigh 1.88g (0.024mol) of acetyl chloride and slowly drop it into the reaction system. After the dropwise addition, the reaction was carried out at room temperature for 3 hours. Afterwards, the reaction solution was poured into a separatory funnel, and an appropriate amount of water and dichloromethane were added thereto for extraction three times. The dichloromethane layer was washed with water once, and the washed water layer was extracted with dichloromethane once again, the organic layers were combined, the extract was dried over anhydrous sodium sulfate, the solvent was r...

Embodiment 3

[0048] The preparation method of 6,7-dibromo-1,2,3,4-tetrahydroisoquinoline of the present embodiment is as follows:

[0049] (1) Synthesis of N-acetyl 1,2,3,4-tetrahydroisoquinoline

[0050] Take a 100ml single-necked bottle, add 2.66g (0.02mol) of 1,2,3,4-tetrahydroisoquinoline, and add 100mL of dichloromethane, stir to dissolve, and then add 2.42g (0.024mol) of triethylamine , after stirring evenly, weigh 1.73g (0.022mol) of acetyl chloride and slowly drop it into the reaction system. After the dropwise addition, the reaction was carried out at room temperature for 3 hours. Afterwards, the reaction solution was poured into a separatory funnel, and an appropriate amount of water and dichloromethane were added thereto for extraction three times. The dichloromethane layer was washed with water once, and the washed water layer was extracted with dichloromethane once again, the organic layers were combined, the extract was dried over anhydrous sodium sulfate, the solvent was r...

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Abstract

The invention discloses a novel compound-6, 7-dibromo-1, 2, 3, 4-tetrahydroisoquinoline and a preparation method thereof. The preparation method includes: adding 1, 2, 3, 4-tetrahydroisoquinoline into a dichloromethane solution, adding triethylamine, adding acetyl chloride, and allowing reaction at 0-5 DEG C for 2-3 h to obtain N-acetyl 1, 2, 3, 4- tetrahydroisoquinoline; suspending N-acetyl 1, 2, 3, 4- tetrahydroisoquinoline in a concentrated sulfuric acid solution, adding N-bromosuccinimide, and allowing reaction at 60-80 DEG C for 1-2 h to obtain N-acetyl-6, 7-bromine- tetrahydroisoquinoline; dissolving N-acetyl-6, 7-bromine- tetrahydroisoquinoline in methanol, adding potassium carbonate, and allowing reaction at 80-90 DEG C for 10-12 h to obtain 6, 7-dibromo-1, 2, 3, 4-tetrahydroisoquinoline. The preparation method is relatively mild in reaction condition, and 6, 7-dibromo-1, 2, 3, 4-tetrahydroisoquinoline is easy to treat and purify and suitable for mass preparation.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a novel compound 6,7-dibromo-1,2,3,4-tetrahydroisoquinoline and a preparation method thereof. Background technique [0002] Tetrahydroisoquinoline compounds have very diverse pharmacological activities, such as strong antihypertensive, antiarrhythmic, antithrombotic activities, etc. Many drug molecules and natural products contain tetrahydroisoquinoline structures or fragments , and thus tetrahydroisoquinoline derivatives are important drug intermediates. However, the synthesis of tetrahydroisoquinolines is mostly achieved through ring closure of phenethylamine molecules. The steps are long, the raw materials are expensive, difficult to operate and the yield is not high, which greatly limits the use of halogenated tetrahydroisoquinolines. Efficient preparation and application requirements of quinoline. In particular, there are few reports on the types and s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D217/02
CPCC07D217/02
Inventor 靳清贤方少明李璐璐张悦凝丁瑞敏李恩洋孙全龙王文玲
Owner ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
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