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Synthesis method of N,N-diisopropyl quadrol

A technology of propylethylenediamine and a synthesis method, applied in the N field, can solve the problems of large amount of waste water, polluted environment, difficult treatment and the like, and achieves the effects of cheap raw materials, simple operation and mild reaction conditions

Active Publication Date: 2011-11-23
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has a high yield, but each step of the reaction needs to be carried out at high temperature, and the energy consumption is high; in the reaction, aluminum trichloride is used, and the amount of waste water is large, difficult to handle, and pollutes the environment

Method used

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  • Synthesis method of N,N-diisopropyl quadrol
  • Synthesis method of N,N-diisopropyl quadrol
  • Synthesis method of N,N-diisopropyl quadrol

Examples

Experimental program
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Effect test

Embodiment 1

[0038] Embodiment 1: the synthesis of diisopropylamino propionamide

[0039] Michael addition reaction: In a 500mL three-necked flask, add 71g (1mol) of acrylamide and 100mL of xylene, mechanically stir at room temperature, add 151.5g (1.5mol) of diisopropylamine dropwise, and control the rate of addition so that the reaction system does not heat up significantly. After the addition was completed, the temperature was raised to 120°C to continue the reaction for 3 hours. The reaction liquid was washed with 30 mL of saturated brine × 3 water, dried with 10 g of anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent to obtain 86.7 g of diisopropylaminopropionamide, a colorless liquid, yield 50.4% (based on the amount of acrylamide substance, the same as in the following examples).

Embodiment 2

[0040] Embodiment 2: the synthesis of diisopropylamino propionamide

[0041]Michael addition reaction: In a 1000mL three-necked flask, add 71g (1mol) of acrylamide and 300mL of methanol, mechanically stir at room temperature to dissolve, add 151.5g (1.5mol) of diisopropylamine dropwise, and control the rate of addition so that the reaction system does not heat up significantly. After the addition, add 3.29g (0.01mol) ammonium dicyclohexyltrifluoromethanesulfonate, raise the temperature to 50°C and react for 48h, add 200mL ethyl acetate after the reaction solution is concentrated, wash the organic layer with 70mL×3 saturated saline, and wash the organic layer with 10g Dry over sodium sulfate, concentrate under reduced pressure to remove the solvent to obtain 141.8 g of diisopropylaminopropionamide, a colorless liquid, and the yield is 82.4%.

Embodiment 3

[0042] Embodiment 3: the synthesis of diisopropylamino propionamide

[0043] Michael addition reaction: In a 2000mL three-necked flask, add 71g (1mol) of acrylamide and 500mL of acetonitrile, mechanically stir at room temperature to dissolve, add 252.5g (2.5mol) of diisopropylamine dropwise, and control the rate of addition so that the reaction system does not heat up significantly. Add complete, add 36.3g (0.1mol) Zn (OTf) 2 , heated to 70°C and reacted for 56 hours, concentrated the reaction solution, added 400 mL of ethyl acetate, washed with 100 mL of saturated brine × 3, dried with 10 g of anhydrous sodium sulfate, concentrated under reduced pressure to remove the solvent to obtain 131.5 g of diisopropylaminopropionamide, light yellow Liquid, yield 76.5%.

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Abstract

The invention discloses a synthesis method of N,N-diisopropyl quadrol. According to the synthesis method, N,N-diisopropyl quadrol is synthesized through Michael addition and Hoffmann degradation by taking acrylamide and diisopropylamine as starting raw materials. The synthesis method has the advantages of advanced process route, reasonable process condition, cheap and available raw materials, mild reaction conditions, high atom economy, low production cost and less three wastes, is simple and safe to operate, is suitable for industrial production, and has a large implementation value and large social and economic benefits.

Description

(1) Technical field [0001] The invention relates to the synthesis of a pharmaceutical intermediate, in particular to a synthesis method of N,N-diisopropylethylenediamine. (2) Background technology [0002] N,N-Diisopropylethylenediamine is a key intermediate in the synthesis of pramiracetam and other drugs. Pramiracetam is a high-efficiency, low-toxic, and well-tolerated cognition activator, which is suitable for the attention and memory impairment of the elderly, benign aging amnesia, senile dementia (Alzheimer's disease) and other diseases The treatment and prevention of the drug, which was first launched in Italy in 1993. The synthesis of pramiracetam is usually obtained by intramolecular condensation of cyclobutyrolactam, chloroacetyl chloride or ethyl chloroacetate and N,N-diisopropylethylenediamine as raw materials. [0003] [0004] This shows that N, N-diisopropylethylenediamine is the key intermediate of synthetic pramiracetam, and its structure is as shown in ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/10C07C209/58
Inventor 谢媛媛刘俊丽夏建胜施湘君苏为科
Owner ZHEJIANG UNIV OF TECH
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