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A Simple Synthesis Method of 9,10-Dimethoxy-1,3,4,6,7,11b-Hexahydro-3-isobutyl-2h-Benzo[a]quinazin-2-one

A technology of dimethoxyl and synthetic method, which is applied in the field of drug synthesis, can solve the problems of unsuitable industrial application, cumbersome operation steps, and long reaction time, and achieve the effect of green synthesis process, cumbersome operation, and long reaction time

Active Publication Date: 2011-11-30
JIANGSU INST OF NUCLEAR MEDICINE +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the process of actual operation, the synthesis method of the prior art has expensive raw materials, long reaction time, cumbersome operation steps, easy to cause environmental pollution, and cannot be widely used in industry

Method used

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  • A Simple Synthesis Method of 9,10-Dimethoxy-1,3,4,6,7,11b-Hexahydro-3-isobutyl-2h-Benzo[a]quinazin-2-one

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Experimental program
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Effect test

Embodiment 1

[0034] The synthesis steps of 9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-3-isobutyl-2H-benzo[a]quinazin-2-one are as follows:

[0035] 1) Mix 75 mmol of formaldehyde, 50 mmol of 40% dimethylamine aqueous solution (the dimethylamine aqueous solution is calculated as dimethylamine), 150 mmol of 5-methyl-2-hexanone, and 100 mmol of hydrochloric acid in 100 mL of ethanol Reflux for 5 h.

[0036] 2) Concentrate the reaction solution from step 1) until there is no liquid. Add 100 mL each of water and diethyl ether, discard the ether layer, alkalinize the aqueous layer with 10% NaOH solution to pH 8, then extract with 100 mL diethyl ether, and concentrate the organic phase under reduced pressure to obtain a colorless liquid.

[0037] 3) The above colorless liquid was purified by column chromatography to obtain the compound 3-dimethylaminomethyl-5-methyl-hexan-2-one (I). The purification steps of column chromatography technology are as follows: Weigh silica gel with a mass 50 times that o...

Embodiment 2

[0042] The synthesis steps of 9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-3-isobutyl-2H-benzo[a]quinazin-2-one are as follows:

[0043] 1) Mix 100 mmol formaldehyde, 50 mmol 40% dimethylamine aqueous solution (dimethylamine aqueous solution is calculated as dimethylamine), 200 mmol 5-methyl-2-hexanone, 90 mmol hydrochloric acid in 120 mL ethanol Reflux for 5 h.

[0044] 2) Concentrate the reaction solution from step 1) until there is no liquid. Add 120 mL each of water and diethyl ether, discard the ether layer, alkalinize the aqueous layer with 10% NaOH solution to pH 9, then extract with 120 mL diethyl ether, and concentrate the organic phase under reduced pressure to obtain a colorless liquid.

[0045] 3) The above colorless liquid was purified by column chromatography to obtain the compound 3-dimethylaminomethyl-5-methyl-hexan-2-one (1). The purification steps of column chromatography technology are as follows: Weigh silica gel with a mass 55 times that of the crude product o...

Embodiment 3

[0050] The synthesis steps of 9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-3-isobutyl-2H-benzo[a]quinazin-2-one are as follows:

[0051] 1) Mix 100 mmol formaldehyde, 50 mmol 40% dimethylamine aqueous solution (the dimethylamine aqueous solution is calculated as dimethylamine), 250 mmol 5-methyl-2-hexanone, 90 mmol hydrochloric acid in 130 mL ethanol Reflux for 5 h.

[0052] 2) Concentrate the reaction solution from step 1) to dryness. Add 100 mL each of water and diethyl ether, discard the ether layer, alkalinize the aqueous layer with 10% NaOH solution to pH 9, then extract with 100 mL diethyl ether, and concentrate the organic phase under reduced pressure to obtain a colorless liquid.

[0053] 3) The above colorless liquid was purified by column chromatography to obtain the compound 3-dimethylaminomethyl-5-methyl-hexan-2-one (1). The purification steps of column chromatography technology are as follows: Weigh silica gel with a mass 55 times that of the crude product of 3-dimeth...

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Abstract

The invention discloses a simple and convenient synthesis method of 9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-3-isobutyl-2H-benzo[a] quinolizidine-2-ketone. According to the invention, easy raw material source is obtained; the preparation cost of the medicine is largely saved by using cheap and easily obtained 5-methyl-2-hexanone as raw material; and the structures of an immediate and a target compound are certified through verifications of nuclear magnetic resonance spectrum, mass spectrum, infrared spectrum and the like; the simple and convenient synthesis method of the 9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-3-isobutyl-2H-benzo[a] quinolizidine-2-ketone, disclosed by the invention, has the advantages of simplified synthesis process, two-step reaction, mild condition for the synthesis method, short reaction time, simplicity and convenience in operation and easiness in separation and purification; the shortcomings in the prior art are also avoided; the green synthesis process has the advantages of mild condition, simplicity and convenience in operation and environment friendliness; and a green synthesis way is provided for the synthesis of the 9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-3-isobutyl-2H-benzo[a] quinolizidine-2-ketone.

Description

technical field [0001] The invention relates to a simple and convenient method of 9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-3-isobutyl-2H-benzo[a]quinazin-2-one A synthesis method belongs to the field of drug synthesis. Background technique [0002] 9,10-Dimethoxy-1,3,4,6,7,11b-hexahydro-3-isobutyl-2H-benzo[a]quinazin-2-one is used in the treatment of Huntington's disease (Huntington's disease, HD) drug, trade name Xenazine (tetrabenazine), in August 2008, approved by the U.S. Food and Drug Administration (FDA) for fast-track approval, becoming the first and only drug approved for use in the U.S. Medications to treat HD. HD is a genetic degenerative brain disease characterized by personality changes, emotional instability, slurred speech, involuntary movements, and drunkenness. It usually develops in middle age and causes mental retardation due to the death of cells in the caudate nucleus , balance ability, language ability and emotional control decline. At present, the dru...

Claims

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Application Information

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IPC IPC(8): C07D455/06
Inventor 李晓敏陈正平刘春仪唐婕陆春雄蒋泉福
Owner JIANGSU INST OF NUCLEAR MEDICINE
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