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The preparation method of proline ester hydrochloride

A technology of proline and hydrochloride, applied in organic chemistry and other directions, can solve the problems of large three wastes, violent reaction, poor atom economy, etc., and achieve the effects of less discharge of three wastes, simple post-processing, and low cost of raw materials

Active Publication Date: 2018-08-14
MAANSHAN DEHONG BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the yield of this method is high, due to SOCl 2 High activity, violent reaction, low temperature operation, and SOCl 2 It is highly toxic and emits a molar amount of SO 2 , the three wastes are large, the atomic economy is poor, and the environmental pollution is serious

Method used

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  • The preparation method of proline ester hydrochloride
  • The preparation method of proline ester hydrochloride
  • The preparation method of proline ester hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1, a kind of preparation method of proline ester hydrochloride, take proline and methyl alcohol as raw material, carry out following steps successively:

[0031] 1), initial reaction, carry out following steps successively:

[0032] ①. Put 11.5g (0.1mol) proline, 30ml dichloroethane and 0.79g (0.01mol) Py (pyridine) into a 250ml three-necked flask, and feed hydrogen chloride gas at a rate of 1.25ml / s (0.5h During the reaction time, hydrogen chloride gas has been fed at this rate), reacted at room temperature for 0.5 h, and consumed 0.1 mol of HCl.

[0033] ②. Afterwards, put 4.16g (0.13mol) methanol into the three-necked flask, and pass in hydrogen chloride at 0.05ml / s (the hydrogen chloride gas has been passed in at this rate during the reaction time of 3h) to keep the hydrochloride of proline. form, react under reflux conditions (about 84 ° C), distill off the dichloroethane containing water (that is, the mixed solution that is distilled from the azeotropi...

Embodiment 2～ Embodiment 10

[0051] Change the following reaction conditions in embodiment 1: select solvent (abbreviation s), alcohol (Acohol), catalyst (Cat), HCl total consumption (abbreviation M), solvent consumption (V), reaction time (abbreviation t), obtain implementation Example 2~10, thereby obtain the product quality (w) of corresponding proline ester hydrochloride, the product yield is called for short (y). See Table 1 for details and data results.

[0052] Table 1

[0053]

[0054]

[0055]

[0056] instruction manual:

[0057] When alcohol is methyl alcohol, gained product is proline methyl ester hydrochloride;

[0058] When alcohol is ethanol, the product obtained is proline ethyl ester hydrochloride;

[0059] When the alcohol is propanol, the resulting product is proline propyl ester hydrochloride.

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Abstract

The invention discloses a preparation method of proline ester hydrochloride. The method sequentially comprises the following steps of 1, an initial reaction is performed, wherein proline, a solvent and a pyridine catalyst are injected into a container, hydrogen chloride gas is introduced, a reaction is performed at room temperature to produce proline ester hydrochloride; then, alcohol is injected into the container, then, hydrogen chloride gas continues to be introduced, the reaction is performed under the reflux temperature, rotary evaporation is performed on a reaction solution, recrystallization and cooling are performed to separate out solid, the solvent is used for washing and filtering, filter cakes are dried, and the proline ester hydrochloride is obtained; the filtrate is subjected to rotary evaporation and used as a mother solution of the next circulation; 2, circulation mechanical application, wherein the solvent in the first step is changed to occupy 0.5-0.7 time of the solvent by volume, the mother solution obtained in the first step is used for replacing the pyridine catalyst in the first step, the other components are the same as the first step, preparation of the proline ester hydrochloride is performed, and therefore circulation mechanical application is achieved.

Description

technical field [0001] The present invention relates to the preparation method of organic compound proline ester hydrochloride. Background technique [0002] Proline methyl ester hydrochloride, molecular formula: C 6 h 12 ClNO 2 , the pure product is a white solid. At present, the main synthesis method is to use thionyl chloride as the chlorination agent, and then form an ester with alcohol. [0003] For example, in England and Wales patent 1072954, using proline and methanol, in SOCl 2 The method for the synthesis of proline methyl ester hydrochloride under the effect of: under ice-bath condition, the proline of molar ratio 1:1 and SOCl 2 , reacted in methanol for 24h, and then the product was obtained after vacuum removal of low boilers, and the yield was 98%. Although this method has a higher yield, due to SOCl 2 High activity, violent reaction, low temperature operation, and SOCl 2 It is highly toxic and emits a molar amount of SO 2 , the three wastes are large,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/16
CPCC07D207/16
Inventor 祁超高锐葛新杨建平
Owner MAANSHAN DEHONG BIOTECH