Method for preparing byproduct N-benzylphthalimide during preparation of mono-propargylamine

A technology of benzyl phthalimide and phthalimide, which is applied in the field of by-product N-benzyl phthalimide, can solve the problems of difficult recovery of by-products, environmental pollution, production High cost and other issues, to achieve the effect of cost reduction, environmental pollution reduction and high yield

Inactive Publication Date: 2009-12-09
夏成才
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In order to overcome the disadvantages of using solvents in the existing propargylamine preparation method, the by...

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] N-propynyl-phthalimide: 185g (1.0mol), benzylamine: 26.8g160.5g (1.5mol), catalyst benzylamine hydrochloride: 14.3g (0.1mol), put into 500ml three ports in the flask. Stir mechanically, and heat the oil bath to 160°C. Fractions around 83°C were collected. The reaction was stopped when the temperature of the distillation head dropped to 65°C. 7.48 g of the product propargyl amine was obtained, and the yield was 68%. Replace the collection bottle with a new one, cool down to about 120°C, and distill off about 39 g of excess benzylamine under reduced pressure. Then change the distillation device to a reflux device, add an appropriate amount of ethanol, and continue to cool down to about 80°C to a slight boiling state, continue to add ethanol until it just dissolves, filter while it is hot, cool the filtrate to about 5°C and filter to obtain N-benzyl Phthalimide 190g, content 95%.

Embodiment 2

[0014] N-propynyl-phthalimide: 185g (1.0mol), benzylamine: 26.8g160.5g (1.5mol), catalyst benzylamine hydrochloride: 14.3g (0.1mol), put into 500ml three ports in the flask. Stir mechanically, and heat the oil bath to 160°C. Fractions around 83°C were collected. The reaction was stopped when the temperature of the distillation head dropped to 65°C. 7.48 g of the product propargyl amine was obtained, and the yield was 68%. Replace the collection bottle with a new one, cool down to about 120°C, and distill off about 39 g of excess benzylamine under reduced pressure. Then change the distillation device to a reflux device, add an appropriate amount of methanol, continue to cool down to about 80°C, and become a slightly boiling state, continue to add methanol until it just dissolves, filter while it is hot, cool the filtrate to about 5°C and filter to obtain N-benzyl Phthalimide 182g, content 95%.

Embodiment 3

[0016] N-propynyl-phthalimide: 185g (1.0mol), benzylamine: 26.8g160.5g (1.5mol), catalyst benzylamine hydrochloride: 14.3g (0.1mol), put into 500ml three ports in the flask. Stir mechanically, and heat the oil bath to 160°C. Fractions around 83°C were collected. The reaction was stopped when the temperature of the distillation head dropped to 65°C. 7.48 g of the product propargyl amine was obtained, and the yield was 68%. Replace the collection bottle with a new one, cool down to about 120°C, and distill off about 39 g of excess benzylamine under reduced pressure. Then change the distillation device to a reflux device, add an appropriate amount of isopropanol, and then continue to cool down to about 80°C to a slight boiling state, continue to add isopropanol until it just dissolves, filter while it is hot, and cool the filtrate to about 5°C and filter to obtain N-benzylphthalimide 173g, content 95%.

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Abstract

The invention provides a method for preparing byproduct N-benzylphthalimide during the preparation of mono-propargylamine. The method comprises the following steps: reacting N-propinyl-phthalimide with high boiling amine at 160-180 DEG C by using amine salt as catalyst, collecting the fraction at 80-85 DEG C, namely, propargylamine, recycling benzylamine from the reaction solution, and then recycling byproduct N-benzylphthalimide from the obtained solution by recrystallisation. The beneficial effect of the invention is as follows: solvent is not used; the yield is high; and compared with existing methods, the method for recycling by-product N-benzylphthalimide through recrystallisation reduces the cost greatly and decreases the environmental pollution.

Description

technical field [0001] The invention relates to a method for producing N-benzyl phthalimide by-product in the preparation process of propargyl amine. Background technique [0002] Propargylamine is an important pharmaceutical intermediate. Existing literature reports that propargylamine can be synthesized by N-propynyl-phthalimide in solvents such as carbitol and benzylamine (equal high boiling point amine), and the reaction temperature is 140-170 ° C. The highest yield is 95%. This preparation method needs to use specific solvent, and byproduct N-benzyl phthalimide is dissolved in the solvent of high boiling point and is difficult to reclaim, has the high production cost (documentation report every production 1 ton of propargylamine uses diethylene glycol two 4.7 tons of butyl ether, the unit price of diethylene glycol dibutyl ether is 52,000 / ton, a total of 244,000 yuan; 3.7 tons of N-benzyl phthalimide, N-benzyl ortho The unit price of phthalimide is 70,000 / ton, about ...

Claims

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Application Information

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IPC IPC(8): C07C211/23C07C209/22C07D209/48
CPCY02P20/584
Inventor 夏成才
Owner 夏成才
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