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Method for preparing N-benzyl-3-pyrrolidone

A technology of pyrrolidone and benzyl, which is applied in the field of preparation of N-benzyl-3-pyrrolidone, can solve the problems of low yield and many steps, and achieves the effect of fewer synthesis steps and high yield

Active Publication Date: 2011-05-18
ZHANGJIAGANG HICOMER CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This synthetic method not only has many steps; and the yield is not high, the closed-loop yield: 65%, the decarboxylation yield: 85%, and the total yield of the two steps is only 55.3%.

Method used

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  • Method for preparing N-benzyl-3-pyrrolidone
  • Method for preparing N-benzyl-3-pyrrolidone
  • Method for preparing N-benzyl-3-pyrrolidone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] a) Synthesis of ethyl 3-benzylaminopropionate:

[0021] Add benzylamine (50.0 g, 0.467 g) into the reactor, under mechanical stirring, control the temperature ≤ 30 °C, add ethyl acrylate (82 mL, 0.766 mol) dropwise, keep the temperature at 35 °C, and stir for 15 h , gas chromatographic monitoring of the reaction raw material ethyl acrylate reaction is complete, stop stirring, distill the reaction liquid, collect 70~75 ℃ / 6mmHg fraction as excess benzylamine, collect 140~142 ℃ / 6mmHg colorless liquid as reaction product 3 -Ethyl benzylaminopropionate, yield: 96.4%;

[0022] b) Synthesis of ethyl 3-(N-ethoxycarbonylmethylene)benzylaminopropionate:

[0023] To the reactor, add ethyl 3-benzylaminopropionate (51.2 g, 0.448 mol), potassium iodide (1.3 g, 7.6 mmol), potassium carbonate (71.2 g, 0.515 mol) and ethyl chloroacetate (77 mL, 0.730 mol), stirred at room temperature for 48 h, LC-Ms monitored the reaction process, filtered after the reaction, collected the filtrate, ...

Embodiment 2

[0030] a) Synthesis of ethyl 3-benzylaminopropionate:

[0031] Add benzylamine (172.3 g, 1.608 mol) into the reactor, under mechanical stirring, control the temperature ≤ 30 °C, add ethyl acrylate (337 mL, 3.168 mol) dropwise, keep the temperature at 40 °C, and stir for 16 h , gas chromatographic monitoring of the reaction raw material ethyl acrylate reaction is complete, stop stirring, distill the reaction liquid, collect 70~75 ℃ / 6mmHg fraction as excess benzylamine, collect 140~142 ℃ / 6mmHg colorless liquid as reaction product 3 - Ethyl benzylaminopropionate; Yield: 95.9%;

[0032] b) Synthesis of ethyl 3-(N-ethoxycarbonylmethylene)benzylaminopropionate:

[0033] To the reactor, add ethyl 3-benzylaminopropionate (174.3 g, 1.528 mol), potassium iodide (4.8 g, 0.029 mol), potassium carbonate (274.5 g, 1.986 mol) and ethyl chloroacetate (283 mL, 2.674 mol), stirred at room temperature for 50 h, LC-Ms monitored the reaction progress, filtered after the reaction, collected the f...

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Abstract

The invention discloses a method for preparing N-benzyl-3-pyrrolidone. The method comprises the following steps of: (a) synthesizing 3-benzylamine ethyl propionate; (b) synthesizing 3-(N-carbethoxy methylene) benzylamine ethyl propionate; (c) synthesizing N-benzyl-4-carbethoxy-3-pyrrolidone; and (d) synthesizing N-benzyl-3-pyrrolidone. The preparation method of the N-benzyl-3-pyrrolidone has the advantages of fewer synthesis steps and high yield.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of N-benzyl-3-pyrrolidone. Background technique [0002] 3-Aminopyrrolidine is an important fine chemical intermediate, widely used in the synthesis of fine chemicals, and its various derivatives are intermediates for the synthesis of pesticides and pharmaceuticals such as insecticides and antibacterials. The optically active acetylated derivatives of 3-aminopyrrolidine can be used in the production of agricultural chemicals and pharmaceutical active substances (eg vinylpyrrolidone-cephalosporin derivatives). [0003] In patent 200710011673.7, the preparation method is adopted: benzylamine is first condensed with chloroacetic acid, esterified with ethanol, then condensed with acrylic acid, reacted with sodium ethoxide, ring closed, and decarboxylated to obtain the target product: N-benzyl-3-pyrrolidone. This synthetic method not only has many ste...

Claims

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Application Information

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IPC IPC(8): C07D207/24
Inventor 陈瀚林
Owner ZHANGJIAGANG HICOMER CHEM CO LTD
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