Preparation methods of dibenzyl ethylenediamine and acetate thereof

A technology of dibenzylethylenediamine acetate and dibenzylethylenediamine, which is applied in the field of compound preparation, can solve the problems of large waste water discharge, unsuitability for large-scale production, large unit consumption of benzaldehyde, etc. The effect of convenience, reduced labor intensity and low cost

Inactive Publication Date: 2010-07-14
CHONGQING CITY CHUNRUI PHARMA CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The disadvantages of these two synthetic routes are: the unit consumption of benzaldehyde is large, the condensation yield is between 60%-70%, the cost is high, and the amount of waste water discharge is large
[0015] This route will produce a large amount of hydrochloric acid in the actual reac

Method used

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  • Preparation methods of dibenzyl ethylenediamine and acetate thereof
  • Preparation methods of dibenzyl ethylenediamine and acetate thereof
  • Preparation methods of dibenzyl ethylenediamine and acetate thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1: Add 240ml of ethanol and 400g of benzaldehyde into a three-necked reaction flask, stir to raise the temperature to 45°C, add 120g of ethylenediamine dropwise, after the dropwise addition, keep the reaction at 40-60°C for 1-1.5 hours, then cool down to 10°C, Filter to get the Schiff base. Dissolve all the Schiff base obtained in the previous reaction into 240ml of ethanol, add it to a 1000L hydrogenation reactor, then add 4g of palladium carbon with a palladium content of 5-10%, control the hydrogen pressure at 5-10kPa, stir and heat up to 60 ℃, react with hydrogen until no hydrogen is absorbed. The solvent after the hydrogenation reaction is completed is filtered to obtain an ethanol solution of dibenzylethylenediamine. The ethanol solution of dibenzylethylenediamine was distilled to dryness, and the ethanol solvent was removed to obtain dibenzylethylenediamine solid. Alternatively, filter the dibenzylethylenediamine ethanol solution after the hydrogenation...

Embodiment 2

[0042] Example 2: Add 240ml of methanol and 400g of benzaldehyde into a three-necked reaction flask, stir and raise the temperature to 50°C, add 120g of ethylenediamine dropwise, after the dropwise addition, keep the reaction at 40-60°C for 1-1.5 hours, then cool down to 6°C, Filter to get the Schiff base. Dissolve all the Schiff base obtained in the previous reaction into 240ml of methanol, add it to a 1000L hydrogenation reactor, then add 4g of palladium carbon with a palladium content of 5-10%, control the hydrogen pressure at 5-10kPa, stir and heat up to 65 ℃, react with hydrogen until no hydrogen is absorbed. The solvent after the hydrogenation reaction is completed is filtered to obtain a methanol solution of dibenzylethylenediamine. The methanol solution of dibenzylethylenediamine was distilled to dryness, and the methanol solvent was removed to obtain dibenzylethylenediamine as a solid. Alternatively, filter the dibenzylethylenediamine methanol solution after the hyd...

Embodiment 3

[0043] Example 3: Add 240ml of ethanol and 400g of benzaldehyde into a three-necked reaction flask, stir and raise the temperature to 55°C, add 120g of ethylenediamine dropwise, after the dropwise addition, keep the reaction at 40-60°C for 1-1.5 hours, then cool down to 8°C, Filter to get the Schiff base. Dissolve all the Schiff base obtained in the previous reaction in 240ml of ethanol, add it to a 1000L hydrogenation reactor, then add 12g of Raney nickel, control the hydrogen pressure at 5-10kPa, stir and raise the temperature to 70°C, and let the hydrogen react until no until the hydrogen is absorbed. The solvent after the hydrogenation reaction is completed is filtered to obtain an ethanol solution of dibenzylethylenediamine. The ethanol solution of dibenzylethylenediamine was distilled to dryness, and the ethanol solvent was removed to obtain dibenzylethylenediamine solid. Alternatively, filter the dibenzylethylenediamine ethanol solution after the hydrogenation reactio...

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Abstract

The invention discloses preparation methods of dibenzyl ethylidenediamine and acetate thereof, which relates to the preparation methods of compounds, wherein the preparation method of the dibenzyl ethylidenediamine comprises the following steps: benzaldehyde reacts with ethylidenediamine for dehydrating so as to obtain Schiff base under the condition of existence of alcohol; and the Schiff base is reduced by hydrogen to obtain the dibenzyl ethylidenediamine under the condition of existence of alcohol and a catalyst. The preparation method of the acetate of the dibenzyl ethylidenediamine comprises the following step: glacial acetic acid is directly added to the alcoholic solution of the dibenzyl ethylidenediamine to be salified to obtain the acetate of the dibenzyl ethylidenediamine. The invention has simple process, short time, high product quality, low environment pollution, high conversion rate and low cost.

Description

technical field [0001] The invention relates to a preparation method of a compound, in particular to a preparation method of a pharmaceutical intermediate dibenzylethylenediamine and its acetate. Background technique [0002] Dibenzylethylenediamine acetate is mainly used as a pharmaceutical intermediate for the production of long-acting penicillin V, long-acting penicillin G, long-acting ampicillin, long-acting cephalosporins and other drugs. At present, it is widely used in the world, and the annual domestic and international sales volume is more than 150 tons. [0003] The structural formula of dibenzylethylenediamine is as follows (I): [0004] [0005] See the synthesis of dibenzylethylenediamine reported at present with benzaldehyde, benzylamine, benzyl chloride as starting raw material: [0006] One, take benzaldehyde as the synthetic route of starting raw material as follows: [0007] [0008] [0009] The disadvantages of these two synthetic routes are: ...

Claims

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Application Information

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IPC IPC(8): C07C211/27C07C209/60C07C53/10C07C51/41
Inventor 李明川郝廷艳胡奎朱泽文赵富文
Owner CHONGQING CITY CHUNRUI PHARMA CHEM
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