N-amino-1,2-cyclopentanediformylimine and preparation method thereof

A technology of cyclopentane dicarboximide and cyclopentane o, which is applied in the field of organic N-amino-1, can solve the problems of high reaction cost and cumbersome steps, and achieve the effect of shortening the reaction steps and reducing the production cost

Inactive Publication Date: 2008-08-06
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The main disadvantage of this reaction process is that the steps are cumbersome, and the product can only be obtained after 4 steps of reaction, and the reaction cost is high

Method used

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  • N-amino-1,2-cyclopentanediformylimine and preparation method thereof
  • N-amino-1,2-cyclopentanediformylimine and preparation method thereof
  • N-amino-1,2-cyclopentanediformylimine and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1: A kind of preparation method of N-amino-1,2-cyclopentane dicarboximide, carries out following steps successively:

[0020] In a 250mL three-neck flask equipped with a reflux condenser and mechanical stirring, add 14g of cyclopentane phthalic anhydride and 50mL of methanol, after heating to reflux, slowly add 7mL of 85% hydrazine hydrate aqueous solution dropwise, and continue to reflux after the dropwise addition React for 6 hours.

[0021] After the reaction is over, stop heating, put the reaction solution to a rotary evaporator to distill off the solvent and water under reduced pressure to obtain a viscous liquid, and after cooling to obtain the product N-amino-1,2-cyclopentanedicarboximide, vacuum Dry at 30° C. for 12 hours to obtain 13.5 g of the product with a yield of 87.7%.

Embodiment 2

[0022] Embodiment 2: A kind of preparation method of N-amino-1,2-cyclopentane dicarboximide, carries out following steps successively:

[0023] In a 250mL three-necked flask equipped with a reflux condenser and mechanical stirring, add 14g of cyclopentane phthalic anhydride, 50mL of methanol, and add 7mL of 85% hydrazine hydrate dropwise at room temperature. After the dropwise addition, heat to reflux. The reaction time is 7 Hour.

[0024] After the reaction is over, stop heating, put the reaction solution to a rotary evaporator to distill off the solvent and water under reduced pressure to obtain a viscous liquid, and after cooling to obtain the product N-amino-1,2-cyclopentanedicarboximide, vacuum Dry at 30° C. for 12 hours to obtain 13.2 g of the product with a yield of 85.7%.

Embodiment 3～11

[0025] Embodiments 3-11: By changing the solvent, the concentration of hydrazine hydrate, the dosage of hydrazine hydrate, and the reaction time in the above-mentioned embodiment 1 or 2, corresponding embodiments 3-11 can be obtained. The specific content is shown in Table 1, and the product yield of each embodiment gained is shown in Table 1.

[0026] The concrete data of table 1, embodiment 3~11

[0027] Reality

[0028] 5

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Abstract

The invention discloses an N-amino-1, 2-cyclopentane dicarboximide whose formula is represented as right. The invention also discloses a corresponding preparation method which comprises using cyclopentane ortho-anhydride as raw material, carrying out hydrazine hydrate in solvent for refluxing reaction for 0.5-12h while the mol ratio of cyclopentane ortho-anhydride and hydrazine hydrate is 1:1-2.5, removing solvent after reaction, and drying to obtain N-amino-1, 2-cyclopentane dicarboximide. The N-amino-1, 2-cyclopentane dicarboximide can be used as the intermediate of gliclazide, thereby reducing the reaction route of gliclazide to reduce waste.

Description

technical field [0001] The invention relates to an organic substance N-amino-1,2-cyclopentane dicarboximide and its chemical synthesis method. Background technique [0002] N-amino-1,2-cyclopentanedicarboximide is a key intermediate for the preparation of Gliclazide. Gliclazide is a second-generation sulfonylurea oral hypoglycemic drug, which has dual effects of lowering blood sugar and improving blood coagulation function, and is widely used clinically. The synthesis of gliclazide usually uses cyclopentane phthalimide as raw material, and LiAlH in tetrahydrofuran 4 Reaction, reduction to obtain azanitrogen ring (Griot, R.SiegfriedAkt.-Ges., Zofingen, Switz.Helvetica Chimica Acta.1959, 42:67-72); dissolve this substance in acetic acid and react with sodium nitrite to obtain N- Nitroso-3-azabicyclooctane is then reduced by zinc powder to obtain hexahydro-2-cyclopentapyrrolylamine (JP05065270A), and finally condensed with p-toluenesulfonylurea to obtain the product (JP060410...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/52
Inventor 陈新志龚灵刘妍钱超
Owner ZHEJIANG UNIV
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