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Preparation method of 3-methyl-7-propylxanthine

A technology of propylxanthine and methylxanthine, applied in the direction of organic chemistry, can solve the problems of unsuitability for industrial production, harsh reaction conditions, strong acidity, etc., and achieve good economic benefits, simple reaction steps, and easy operation

Inactive Publication Date: 2012-10-10
CSPC INNOVATION PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The above synthesis method needs two steps, the reaction conditions are harsh, the temperature is high, and the acidity is strong, and the starting material 4-methylamino-5 carbamic acid-1 propylimidazole used has high cost and is not suitable for industrial production

Method used

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  • Preparation method of 3-methyl-7-propylxanthine
  • Preparation method of 3-methyl-7-propylxanthine
  • Preparation method of 3-methyl-7-propylxanthine

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Add 16.6g (100mmol) of 3-methylxanthine, 14g (101mmol) of potassium carbonate, 0.83g (5mmol) of potassium iodide, and 330g (4.5mol) of DMF into a 500ml four-necked flask, heat to 45°C, and dropwise add 7.4g of bromopropane (60mmol), the dropwise addition time is 20min, after the dropwise addition, the temperature is raised to 90°C and kept for 1h.

[0027] After the reaction, the DMF was distilled off to obtain the crude product. After dissolving the crude product with 1mol / L sodium hydroxide solution, add 1 g of activated carbon, keep it warm at 80°C for 0.5h, and filter; add hydrochloric acid to the filtrate to adjust the pH to 5, and cool to 0°C. Suction filtration; add a small amount of water to the filter cake, stir and heat up to 60°C, add sodium hydroxide solution to dissolve it. Add 1 g of activated carbon, incubate at 80°C for 1 hour, decolorize, and filter; add hydrochloric acid to the filtrate to adjust pH to 5, cool to 0°C, filter with suction, and dry to ob...

Embodiment 2

[0029] Add 44g (265mmol) of 3-methylxanthine, 28.3g (267mmol) of sodium carbonate, 1.3g (13mmol) of sodium bromide, and 352g (4.8mol) of DMF into a 500ml four-neck flask, heat to 60°C, drop 65.2 g (530 mmol) of bromopropane, the time for the dropwise addition is 40 minutes, after the addition, the temperature is raised to 100°C, and the temperature is kept for 2.5 hours.

[0030] After the reaction, the DMF was distilled off to obtain the crude product. After the crude product was dissolved with 1mol / L sodium hydroxide solution, 1 g of activated carbon was added, and kept at 80°C for 2 hours, decolorized, and filtered while it was hot; the filtrate was adjusted to pH 7 by adding hydrochloric acid, and cooled to Suction filtration at 45°C; stir the filter cake with a small amount of water, heat up to 60°C, add sodium hydroxide solution to dissolve it. Add 1 g of activated carbon, keep warm at 80°C for 1 hour, decolorize, and filter while hot; add hydrochloric acid to the filtra...

Embodiment 3

[0032] Add 49.8g (300mmol) of 3-methylxanthine, 41.5g (301mmol) of potassium carbonate, 1.12g (15mmol) of potassium chloride, and 249g (3.4mol) of DMF into a 500ml four-neck flask, heat to 75°C, drop Chloropropane 47.1g (600mmol), the dropwise addition time is 60min, after the dropwise addition, the temperature is raised to 110°C, and the temperature is kept for 2h.

[0033] After the reaction, the DMF was distilled off to obtain the crude product. After dissolving the crude product with 1mol / L sodium hydroxide solution, add 1 g of activated carbon, keep it at 60°C for 4 hours, decolorize, and filter hot; add sulfuric acid to the filtrate to adjust the pH to 6, and cool down to 20 ℃, filter with suction; add a small amount of water to the filter cake, stir, heat up to 60 ℃, add sodium hydroxide solution to dissolve it. Add 1 g of activated carbon, keep warm at 60°C for 2 hours, decolorize, and heat filter; add sulfuric acid to the filtrate to adjust pH to 6, cool to 25°C and f...

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Abstract

The invention discloses a preparation method of 3-methyl-7-propylxanthine. According to the preparation method, 3-methylxanthine and halogenated propane are subject to condensation reaction in N, N-dimethylformamide solvent by using the mixture of alkali carbonate and alkali halide as a condensating agent so as to obtain 3-methyl-7-propylxanthine, and 3-methyl-7-propylxanthine is purified to obtain the finished product of 3-methyl-7-propylxanthine. The preparation method disclosed by the invention has the advantages of mild condition of reaction, simplicity and convenience in operation, and high yield; and the used raw materials are cheap and easy to obtain; and the product is high in purity.

Description

technical field [0001] The invention relates to the synthesis technology of organic compounds, in particular to a preparation method of 3-methyl-7-propylxanthine. Background technique [0002] 3-Methyl-7-propylxanthine (3-Methyl-7-propylxanthine) is a xanthine compound with the chemical name 3-methyl-7-propyl-3,7-dihydro-1H- Purine-2,6-dione with the molecular formula C 9 h 12 N 4 o 2 , molecular weight 208.22 Daltons, CAS number 55242-64-3, structural formula as follows: [0003] [0004] 3-Methyl-7-propylxanthine is an important pharmaceutical intermediate. Clinical studies have found that 3-methyl-7-propylxanthine has a good effect on improving brain energy metabolism and can promote nerve movement to the brain. [0005] JP19880002066 discloses a synthetic method of 3-methyl-7-propylxanthine. The method uses 4-methylamino-5 carbamic acid-1 propylimidazole (I) and urea to melt at 135~140°C, react for 1~3 hours to obtain the compound shown in formula II, and then ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D473/04
Inventor 刘晖刘琨赵会娟杜亚东谢丽莎
Owner CSPC INNOVATION PHARMA
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