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Synthetic method of alpha-amino aromatic ketone compound

A technology of aminoaromatic ketone and synthesis method, which is applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., can solve problems such as difficult industrial production, complicated operation steps, and many reaction steps, and achieve good industrialization prospects, The effect of high yield and purity and mild reaction conditions

Inactive Publication Date: 2013-08-14
HUBEI UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This technique has the following disadvantages: the reaction steps are many, the procedure is complicated, and it is difficult to realize industrialized production; in the chlorination reaction, except that the α-chlorination reaction product can be generated, many substituted by-products are also generated, which is not conducive to the purification of the product; each step A large amount of waste water is produced in the subsequent treatment of the reaction, polluting the environment
The disadvantage of this method is: the reaction raw material 2-methyl-2-(4-morpholinyl)-1-(4-chlorophenyl)-1-acetone is expensive; the separation of raw material and product is difficult, and the follow-up operation steps complex

Method used

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  • Synthetic method of alpha-amino aromatic ketone compound
  • Synthetic method of alpha-amino aromatic ketone compound

Examples

Experimental program
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Effect test

Embodiment 1

[0035] The synthesis of embodiment 1,2-methyl-2-(4-morpholinyl)-1-phenylacetone

[0036] Add 300ml of benzene and 80g (0.6mol) of aluminum trichloride to a four-neck flask equipped with a thermometer, a drying tube, an electromagnetic stirrer, and a constant pressure dropping funnel. After stirring evenly, add 93g ( 0.5mol) α-bromoisobutyryl chloride, react at room temperature for 9h after the dropwise addition is completed. After the reaction, extract with 1000ml 10% hydrochloric acid aqueous solution to obtain the aqueous phase, then extract with 2×100ml benzene to separate the organic phase. The organic phase was adjusted to pH=7 by washing with 2×100ml saturated sodium bicarbonate solution, and the obtained organic phase was distilled under reduced pressure to -0.096mpa to obtain the intermediate product 2-methyl-2-bromo-1-propiophenone.

[0037] Add 300ml of 60-90℃ petroleum ether, 104g (1.2mol) of morpholine, and 6.7g (0.05mol) of aluminum trichloride into a four-neck f...

Embodiment 2

[0038] Embodiment 2, the synthesis of 2-methyl-2-(diethylamino)-1-phenylacetone

[0039] The synthetic method of the intermediate product 2-methyl-2-bromo-1-propiophenone is the same as in Example 1.

[0040] Add 0.2mol 2-methyl-2-bromo-1-propiophenone, 300ml toluene, 2.7g (0.02mol) trichloride aluminum. 60ml (0.6mol) of diethylamine was added dropwise with stirring. After the dropwise addition, react at 55°C for 16h. After the reaction, toluene and diethylamine were distilled off, then 10% hydrochloric acid aqueous solution was added dropwise to adjust the pH of the reaction solution to 2, and 100ml of toluene was added to stir and stand to separate the water phase. Adjust the pH of the aqueous phase to 10 with saturated sodium carbonate solution. The organic phase was separated by extraction with 2×100ml chloroform, and the crude product was obtained by distillation under reduced pressure to -0.096mpa. Recrystallize with the mixed solvent of ethanol and water subsequent...

Embodiment 3

[0041] Embodiment 3, the synthesis of 2-methyl-2-piperidinyl-1-phenylacetone

[0042] The synthetic method of the intermediate product 2-methyl-2-bromo-1-propiophenone is the same as in Example 1.

[0043] In a four-necked flask equipped with a thermometer, reflux condenser, mechanical stirring, and dropping funnel, add 0.2mol 2-methyl-2-bromo-1-propiophenone, 400ml benzene, 27g (0.2mol) aluminum trichloride . 30ml (0.3mol) of piperidine was added dropwise with stirring. After the dropwise addition, react at 40°C for 6h. After the reaction, benzene and piperidine were distilled off, then 10% hydrochloric acid aqueous solution was added dropwise to adjust the pH of the reaction solution to 2, and 100ml of benzene was added to stir and stand still to separate the water phase. Use saturated sodium carbonate solution to adjust the pH of the aqueous phase to 10, then extract with 2×100ml chloroform to separate the organic phase, and distill under reduced pressure to -0.096mpa to o...

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Abstract

The invention relates to a synthetic method of an alpha-amino aromatic ketone compound. The reaction method comprises step one, reacting benzene or substituted benzene and 2-bromo-isobutyl chloride with a water-insoluble solvent in the presence of a catalyst in the absence of water to generate an intermediate product 2-bromo-2-methyl-1-benzene or substituted propiophenone; and step two, reacting the intermediate product with a compound having a secondary amine structure under an action of an organic solvent and the catalyst, and performing aftertreatment of hydrolysis, extraction and the like to obtain the alpha-amino aromatic ketone compound of which the final yield is up to more than 80 percent and the purity is more than 97 percent. The synthetic method of the alpha-amino aromatic ketone compound is high in yield and product purity, low in environmental pollution and low in cost, and an industrial production requirement of alpha-amino aromatic ketone photoinitiator can be met, so that the possibility is provided for the industrial production of the product.

Description

technical field [0001] The invention relates to a method for synthesizing an ultraviolet photoinitiator-α-amino aromatic ketone compound. Background technique [0002] The α-aminoaryl ketone photoinitiator has better water solubility because it contains an amine group. At the same time, because the amine group can combine with inorganic salts to form salts, the amine photoinitiator is highly reconfigurable. From the initially developed photoinitiator 369 to photoinitiator 379, 907, N-1414, Polymeric 910, the development of amine photoinitiators tends to develop towards macromolecular photoinitiators. Due to its relatively difficult synthesis, especially the photoinitiator 907, there are not many synthetic studies at home and abroad. [0003] (1) foreign synthesis process [0004] Ciba-Geigy company Pretot Roger et al. (WO2006034966) used sulfide anisole as a starting material, and reacted with morpholine to obtain photoinitiator 907 after Friedel-Crafts reaction, halogena...

Claims

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Application Information

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IPC IPC(8): C07D295/108C07C225/16C07C221/00C07C323/32C07C319/20C07D211/32
Inventor 徐保明唐强陈坤熊伟方淼韩洋洋裴智山张杰胡欢
Owner HUBEI UNIV OF TECH
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