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Process for producing 1-ethyl-2-aminomethylpyrrolidine

A technology of aminomethylpyrrolidine and nitromethylenepyrrolidine is applied in the field of 1-ethyl-2-aminomethyl, and can solve the problem of high reaction pressure, high reaction pressure of 1-ethyl-2-aminomethylpyrrolidine, Recycling solvent wastes energy and low reaction yield, and achieves the effect of reducing side reactions, easier recovery, and high catalytic efficiency

Inactive Publication Date: 2017-05-10
JIANGSU KANGHENG CHEM
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  • Summary
  • Abstract
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AI Technical Summary

Problems solved by technology

[0007] In addition to the low conversion rate in the prior art, there are also the following disadvantages: 1) The reaction pressure of 1-ethyl-2-aminomethylpyrrolidine using liquid phase high-pressure reaction is high, dangerous and needs to pass through the process of intermediate products. Separation, resulting in high investment; 2) Using low-carbon alcohol as a solvent, the solvent loss is high, and recycling the solvent is a waste of energy
But still there is certain shortcoming: because 1-ethyl-2-nitromethylenepyrrolidine is unstable, under acidic or alkaline condition, all easily decomposes into 1-ethylpyrrolidone and nitromethane, cause reaction to close low rate

Method used

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  • Process for producing 1-ethyl-2-aminomethylpyrrolidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add 78g (0.5mol) of 1-ethyl-2-nitromethylenepyrrolidine and 300ml of methanol into a 1000ml autoclave, then add catalyst nickel (8g), fill it with nitrogen to a pressure of 5kg, and re-exhaust After three times, add hydrogen at a hydrogen pressure of 35 kg and a temperature of about 80°C until the hydrogen pressure does not decrease. The reaction time is about 4 hours. 49 grams of colorless liquid, yield 77%, GC content ≥ 98.5%.

Embodiment 2

[0025] Add 78g (0.5mol) of 1-ethyl-2-nitromethylenepyrrolidine and 300ml of methanol into a 1000ml autoclave, then add catalyst nickel (8g), fill it with carbon dioxide to a pressure of 5kg, and exhaust the gas After three times, press the carbon dioxide pressure to 10 kg, then add hydrogen at a hydrogen pressure of 35 kg and a temperature of 80°C until the hydrogen pressure does not decrease. The reaction time is about 4 hours. , and then rectify after recovering methanol to obtain 53 grams of colorless liquid, with a yield of 83% and a GC content of ≥99%.

[0026] The following table 1 is a comparison table of the production process of 1-ethyl-2-aminomethylpyrrolidine in Examples 1 to 2 to produce 1-ethyl-2-aminomethylpyrrolidine:

[0027] Example 1 Example 2 stamping nitrogen stamping partial pressure of carbon dioxide Raw material quantity 78g 78g Yield 49g 53g yield 77% 83% GC content ≥98.5% ≥99%

[0028] As can be se...

Embodiment 3

[0030] With reference to Example 2, the catalyst nickel was replaced with 5% palladium carbon (2 grams) as a catalyst, and the other reaction conditions were unchanged. After the treatment, 55 grams of a colorless liquid were obtained, with a yield of 86% and a GC content ≥ 99%.

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Abstract

The invention relates to a process for producing 1-ethyl-2-aminomethylpyrrolidine. An intermediate 1-ethyl-2-nitro-methylene pyrrolidine is taken as a raw material, and 1-ethyl-2-aminomethylpyrrolidine is obtained through catalytic reduction under the action of solvents and a catalyst; and the solvents are an organic solvent and carbon dioxide. The process for producing 1-ethyl-2-aminomethylpyrrolidine has the advantages that the organic solvent and carbon dioxide are adopted as the solvents, 1-ethyl-2-aminomethylpyrrolidine is synthesized by catalytic reduction in the presence of carbon dioxide, side reaction is reduced, the decomposition of 1-ethyl-2-aminomethylpyrrolidine into 1-ethyl-2-pyrrolidinone is reduced, and the product yield and GC content are greatly improved.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, in particular to a 1-ethyl-2-aminomethyl [0002] The production process of pyrrolidine. Background technique [0003] 1-Ethyl-2-aminomethylpyrrolidine, whose structure is shown in formula (I), and whose CAS number is 26116-12-1, is an important organic intermediate, which is a raw material in the pharmaceutical industry and can be used in the production of Psychiatric drugs sulpiride, amisulpiride and levosulpiride, etc. [0004] [0005] (I) [0006] 1-Ethyl-2-aminomethylpyrrolidine is mainly obtained by high-pressure intermittent hydrogenation reduction of intermediate 1-ethyl-2-nitromethylpyrrolidine, low-carbon alcohol as solvent, and Raney nickel as catalyst. [0007] In addition to the low conversion rate in the prior art, there are also the following disadvantages: 1) The reaction pressure and danger of generating 1-ethyl-2-aminomethylpyrrolidine using liquid-phase high-p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/09
CPCY02P20/584C07D207/09
Inventor 邱志刚窦清玉
Owner JIANGSU KANGHENG CHEM
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