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Method for preparing 3-aminopyrrolidine hydrochloride by using one-pot method

A technology of aminopyrrolidine hydrochloride and pyrrole, applied in the field of one-pot preparation of 3-aminopyrrolidine hydrochloride, can solve the problems of no industrial production, high production cost, inconvenient source, etc., and achieve complete reaction transformation, The effect of reducing pollution and reducing the cost of tail gas treatment

Inactive Publication Date: 2018-08-24
NANJING YUANSHU MEDICAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

(Sichuan Chemical Industry. 2012, 2:12-15) This route uses lithium aluminum hydride as a reducing agent, and the raw materials are expensive, resulting in higher production costs
This route has the shortest synthetic route for raw materials, but the raw material 1,2,4-tribromobutane is not industrially produced in China, and the price is expensive and the source is inconvenient

Method used

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  • Method for preparing 3-aminopyrrolidine hydrochloride by using one-pot method
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  • Method for preparing 3-aminopyrrolidine hydrochloride by using one-pot method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1 Weigh 6.70g of pyrrole, 8.8g of acetonitrile, 0.012g of bis(triphenylphosphine)copper nitrate in a 100ml flask, after cooling with ice water, slowly add 16ml of 8mol / L concentrated nitric acid dropwise, react for 1h, concentrate and add 68g of water, 100ml of ethyl acetate for extraction, and the organic layer was separated. Put the organic layer into a 250ml three-necked flask, add 8.52gPd, plug the bottle mouth with a rubber stopper, insert a glass catheter on the rubber stopper, the inlet end goes deep into the bottom of the liquid level, the gas outlet end is higher than the liquid level, and the oil bath is heated to At 80°C, hydrogen gas was slowly introduced for 1.5 hours, and the total amount of hydrogen gas introduced was 0.44 mol. Stop heating, cool to room temperature, add 26.40 g of ethyl acetate, replace the hydrogen source with HCl gas, and continue to feed HCl gas for 5 min at a flow rate of 1 L / min. After the reaction was completed, an appropr...

Embodiment 2

[0027] Example 2 Weigh 6.70g of pyrrole, 8.8g of acetonitrile, and 0.024g of bis(triphenylphosphine)copper nitrate into a 100ml flask, slowly add 18ml of 8mol / L concentrated nitric acid dropwise under ice-water bath cooling conditions, stir magnetically, and react for 1h After the reaction was completed and concentrated, 68 g of water was added, extracted with 100 ml of ethyl acetate, and the organic layer was separated. Put the organic layer into a 250ml three-necked flask, add 9.58g of Pd, plug the bottle mouth with a rubber stopper, insert a glass catheter on the rubber stopper, the inlet end goes deep into the bottom of the liquid level, the gas outlet end is higher than the liquid level, and the oil bath is heated to 85°C, slowly inject hydrogen for 1.5h. Stop heating, cool to room temperature, add 26.40 g of ethyl acetate, replace the hydrogen source with HCl gas, and continue to feed HCl gas for 6 min at a flow rate of 1 L / min. After the reaction was completed, an appr...

Embodiment 3

[0028] Example 3 Weigh 6.70g of pyrrole, 8.8g of acetonitrile, and 0.024g of bis(triphenylphosphine)copper nitrate into a 100ml flask, slowly add 20ml of 8mol / L concentrated nitric acid dropwise under ice-water cooling conditions, stir magnetically, and react for 1h After the reaction was completed and concentrated, 68 g of water was added, extracted with 100 ml of ethyl acetate, and the organic layer was separated. Put the organic layer into a 250ml three-necked flask, add 9.58g of Pd, plug the bottle mouth with a rubber stopper, insert a glass catheter on the rubber stopper, the inlet end goes deep into the bottom of the liquid level, the gas outlet end is higher than the liquid level, and the oil bath is heated to 85°C, slowly inject hydrogen for 1.5h. Stop heating, cool to room temperature, add 26.40 g of ethyl acetate, replace the hydrogen source with HCl gas, and continue to feed HCl gas for 6 min at a flow rate of 1 L / min. After the reaction was completed, an appropria...

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Abstract

The invention discloses a method for preparing 3-aminopyrrolidine hydrochloride by using a one-pot method. Under an ice-water bathing condition, pyrrole is dissolved in acetonitrile, a catalyst di(triphenyl phosphine) cupric nitrate is added at the same time, nitric acid is added dropwise to conduct a reaction to generate reaction liquid containing 3-nitropyrrole, the reaction liquid is subjectedto extraction by water and ethyl acetate, and an organic phase is obtained after separation is conducted; the obtained organic phase is subjected to reduction by pumping in hydrogen gas under the palladium catalysis condition, and a crude product of 3-aminopyrrolidine is obtained; and a solvent ethyl acetate is added into the crude product of 3-aminopyrrolidine, HCl gas is pumped in to conduct a reaction, and 3-aminopyrrolidine hydrochloride is obtained. The experiment route of the method is simple and short, the raw materials are cheap and easy to get, and the reaction condition is mild.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for preparing 3-aminopyrrolidine hydrochloride in one pot. Background technique [0002] 3-aminopyrrolidine is an important fine chemical intermediate, which is widely used in the synthesis of pesticides and medicines, and has a good market prospect. Domestic 3-aminopyrrolidine is mainly used in pharmaceuticals, and quinolone antibacterial drugs such as norfloxacin, clinfloxacin, and ABT-719 with bactericidal effects can be synthesized through 3-aminopyrrolidine. [0003] At present, there are mainly five kinds of synthetic methods: [0004] 1. Using acrylate as raw material, addition of N-ethoxycarbonylglycine ethyl ester to generate diester, Diechmann ring closure reaction to generate N-ethoxycarbonyl-4-ethoxycarbonyl-3-pyrrolidone, hydroxylamine hydrochloride oximation, hydroboration Sodium reduction, hydrolysis and decarboxylation under acidic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/14
CPCC07D207/14
Inventor 金峰周太勇王凯
Owner NANJING YUANSHU MEDICAL TECH CO LTD
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