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Method of preparing 2-(N, N- dimethylamino)-2 phenyl butanol

A technology of dimethylamino and phenylbutanol, applied in chemical instruments and methods, preparation of organic compounds, preparation of aminohydroxy compounds, etc., can solve the problems of low total yield, long reaction steps, etc., and achieves less by-products, The effect of mild reaction conditions and high yield

Active Publication Date: 2014-07-02
BEIJING ODYSSEY CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction steps are long and the overall yield is low

Method used

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  • Method of preparing 2-(N, N- dimethylamino)-2 phenyl butanol
  • Method of preparing 2-(N, N- dimethylamino)-2 phenyl butanol

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Embodiment 1

[0038] 1. Preparation of 2-(N,N-dimethylamino)-2-phenylbutyronitrile: 100g propiophenone (0.75mol), 45g sodium cyanide (0.91mol), 337g40% dimethylamine methanol solution, 140g of water is put into a 1L autoclave, the mouth of the kettle is wiped clean, and the lid of the kettle is closed. After stirring for 30 minutes, the temperature began to rise, and the addition reaction was carried out at a pressure of 0.3 MPa and a temperature of 80° C. for 8 hours. After the reaction is over, turn on the cooling water to cool down to 30°C, open the pressure relief valve to release the pressure; open the autoclave, pour out the material, rinse it with water, add water to a total volume of 1200ml, cool down to 10°C with ice salt water, filter, and use Wash the filter cake with 100ml×2 water (the filtrate and washing liquid are treated with aqueous potassium permanganate solution), and dry the filter cake to obtain 153g of the product, with a content (HPLC) of 99.6%, and a yield of 86.4%; ...

Embodiment 2

[0048]1. Preparation of 2-(N,N-dimethylamino)-2-phenylbutyronitrile: 100g propiophenone (0.75mol), 42g sodium cyanide (0.85mol), 330g40% dimethylamine methanol solution, water 140g, put it into a 1L autoclave, wipe the mouth of the kettle clean, and close the lid of the kettle. After stirring for 30 minutes, the temperature began to rise, and the addition reaction was carried out at a pressure of 0.3 MPa and a temperature of 80° C. for 8 hours. After the reaction is over, turn on the cooling water to cool down to 30°C, open the pressure relief valve to release the pressure; open the autoclave, pour out the material, rinse it with water, add water to a total volume of 1200ml, cool down to 10°C with ice salt water, filter, and use Wash the filter cake with 100ml×2 water (the filtrate and washing liquid are treated with potassium permanganate aqueous solution), and dry the filter cake to obtain 149g of the product, with a content (HPLC) of 99.3%, and a yield of 84.1%.

[0049] 2...

Embodiment 3

[0058] 1. Preparation of 2-(N,N-dimethylamino)-2-phenylbutyronitrile: 100g propiophenone (0.75mol), 45g sodium cyanide (0.91mol), 337g40% dimethylamine methanol solution, 140g of water is put into a 1L autoclave, the mouth of the kettle is wiped clean, and the lid of the kettle is closed. After stirring for 30 minutes, the temperature was raised, and the addition reaction was carried out at a pressure of 0.3 MPa and a temperature of 60° C. for 8 hours. After the reaction is over, turn on the cooling water to cool down to 30°C, open the pressure relief valve to release the pressure; open the autoclave, pour out the material, rinse it with water, add water to a total volume of 1200ml, cool down to 10°C with ice salt water, filter, and use Wash the filter cake with 100ml×2 water (the filtrate and washing liquid are treated with potassium permanganate aqueous solution), and dry the filter cake to obtain 147g of the product, with a content (HPLC) of 99.1%, and a yield of 83%.

[0...

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Abstract

The invention discloses a method of preparing 2-(N, N- dimethylamino)-2 phenyl butanol. The method comprises the following steps: (1), uniformly mixing sodium cyanide, dimethyl amine, propiophenone and water in an organic solvent to carry out addition reaction, and obtaining 2-(N, N- dimethylamino)-2 phenyl butyronitrile after the reaction is ended; (2), hydrolyzing and refluxing the 2-(N, N- dimethylamino)-2 phenyl butyronitrile under the condition with pH value not smaller than 12, and obtaining 2-(N, N- dimethylamino)-2 phenyl butyric acid after the reaction is completed; (3), uniformly mixing and refluxing the 2-(N, N- dimethylamino)-2 phenyl butyric acid with alcohol and concentrated sulfuric acid for esterification, and obtaining 2-(N, N- dimethylamino)-2 phenyl ethyl butyrate after the reaction is completed; and (4), uniformly mixing the 2-(N, N- dimethylamino)-2 phenyl ethyl butyrate with a reducing agent and water to carry out reduction reaction to obtain a target product. The method disclosed by the invention is mild in reaction condition, less in byproducts and high in yield.

Description

technical field [0001] The invention relates to a method for preparing 2-(N,N-dimethylamino)-2-phenylbutanol. Background technique [0002] 2-(N,N-dimethylamino)-2-phenylbutanol is an important intermediate of the gastric motility drug trimebutin, and five synthetic methods have been reported in the literature: [0003] (1) Using propiophenone as a raw material, first react with trimethylsulfoxide iodide to generate 2-ethyl-2-phenyloxirane, and then react with trimethylaluminum and dimethylamine to generate the target product. Although this method has a short route, both intermediates and target products need to be purified by column chromatography, which is not suitable for industrial production. [0004] (2) Using propiophenone as a raw material, first react with trimethylsulfoxide iodide to generate 2-ethyl-2-phenyloxirane, then convert it into 2-oxazoline, and then undergo ring opening and reduction of amine to obtain the target product. The method requires harsh reac...

Claims

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Application Information

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IPC IPC(8): C07C213/00C07C215/28
Inventor 吴细兵刘斌孙洪亮
Owner BEIJING ODYSSEY CHEM
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