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3- methylamino-1-phenylpropanol preparation method

A technology of methylamino and phenylpropanol, which is applied in the field of synthesis of chemical drug intermediates, can solve the problems of high COD value wastewater, difficult solvent recovery, high production costs, etc., achieve less discharge of three wastes, reduce dehydroxylation side reactions, and production costs low effect

Inactive Publication Date: 2008-11-12
SHAOXING ZHONGKE BAIYUN CHEM TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The disadvantages of this preparation method are that the reagents used for potassium borohydride reduction are expensive, the production cost is high, and a large amount of waste water with high COD value is produced; the target product is extracted by solvents with high toxicity and low boiling point such as ether and chloroform, and the solvent has defects such as difficult recovery. , also affects the environment

Method used

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  • 3- methylamino-1-phenylpropanol preparation method
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Examples

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Effect test

Embodiment 1

[0021] 120.0g of acetophenone, 30.0g of paraformaldehyde, and 67.5g of monomethylammonium hydrochloride (molar ratio 1:1:1) were added to a 100ml autoclave, and 500ml of ethanol was added to keep the reaction temperature at 60°C. Samples were taken every 2 hours for liquid phase detection, and the reaction was stopped until the difference in the content of 3-methylamino-1-propiophenone hydrochloride in two adjacent detection results was less than 5%. The volume of the reaction solution was concentrated by heating to about 1 / 3 of the original volume, cooled and crystallized, and filtered to obtain about 121 g of white crystal or slightly yellow solid 3-methylamino-1-propiophenone hydrochloride.

[0022] Add the 3-methylamino-1-propiophenone hydrochloride obtained above into a 1000mL stainless steel autoclave, add water until the solid is completely dissolved, add 6.1g of Raney nickel catalyst, first replace it with nitrogen for 3 times, then use 0.3MPa hydrogen Replace 3 times,...

Embodiment 2

[0024] Add 120.0g of acetophenone, 30.0g of paraformaldehyde, and 101.3g of monomethylammonium hydrochloride (molar ratio 1:1:1.5) into a 1000ml autoclave, and add 500ml of isopropanol to keep the reaction temperature at 90°C , take samples every 2 hours for liquid phase detection, the difference in the content of 3-methylamino-1-propiophenone hydrochloride in two adjacent detection results is less than 5%, and the volume of the heated and concentrated reaction solution is about 1 / 3 of the original volume , cooled and crystallized, and filtered to obtain about 162.7 g of white crystal or slightly yellow solid 3-methylamino-1-propiophenone hydrochloride.

[0025] Add the 3-methylamino-1-propiophenone hydrochloride obtained above into a 1000mL stainless steel autoclave, add water until the solid is completely dissolved, add 16.3g of Raney nickel catalyst, first replace it with nitrogen for 3 times, then use 1.5MPa hydrogen Replace 3 times, control the temperature at 80°C under s...

Embodiment 3

[0027] 120.0g of acetophenone, 45.0g of paraformaldehyde, and 67.5g of monomethylammonium hydrochloride (molar ratio 1:1.5:1) were added to a 1000ml autoclave, and 500ml of ethanol was added to keep the reaction temperature at 90°C. Sampling was carried out at intervals of 2 hours for liquid phase detection, and when the difference in the content of 3-methylamino-1-propiophenone hydrochloride between two adjacent detection results was less than 5%, the reaction liquid was cooled. The volume of the reaction solution was concentrated by heating to about 1 / 3 of the original volume, cooled and crystallized, and filtered to obtain about 170.2 g of white crystal or slightly yellow solid 3-methylamino-1-propiophenone hydrochloride.

[0028] Add the 3-methylamino-1-propiophenone hydrochloride obtained above into a 1000ml stainless steel autoclave, add water until the solid is completely dissolved, add 8.5g of Raney nickel catalyst, and use N 2 Substitute twice, then replace twice with...

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Abstract

This invention discloses a method for producing 3-methylamidol-1-phenylpropanol. Wherein: it uses acetophenone, paraformaldehyde and methylamine salt as raw material, uses alcohol as solvent in a sealed container and heat to 60-100Deg C to carry out the reaction, after condensation obtain the 3-methylamidol-1-propiophenone hydrochlorate by cooling crystallization; then obtain the 3-methylamidol-1-phenylpropanol hydrochlorate solution by reducing reaction under catalyst; adjust the pH to 9-14 using base solution, and obtain 3-methylamidol-1-phenylpropanol by extraction, solvent recovering and cyclohexane recrystallization, wherein Raney-nickel catalysts catalytic hydrogenation reduction is applied in the 3-methylamidol-1-phenylpropanol hydrochlorate solution production. The said Raney-nickel catalysts catalytic hydrogenation reduction condition is: hydrogen gas pressure 0.3-1.5MPa and temperature 25-80Deg C. This invention is characterized of high product yield, high quality, low cost, and few three waste discharging.

Description

technical field [0001] The invention belongs to the field of synthesis of chemical drug intermediates, and more specifically relates to a preparation method of 3-methylamino-1-phenylpropanol. Background technique [0002] Fluoxetine is a drug developed by Eli Lilly and Company of the United States and launched in 1987 as a drug for treating depression. Currently, it is mostly fluoxetine hydrochloride on the market. Product 3-methylamino-1-phenylpropanol is a key intermediate for the synthesis of antidepressant drug fluoxetine (Fluooxetine, trade name Prozac), and its structural formula is as follows: [0003] [0004] 3-Methylamino-1-phenylpropanol Fluoxetine Hydrochloride [0005] For example, in March 1996, "Chinese Journal of Medicinal Chemistry", Volume 6, No. 1, Page 56-57, Huang Yanhe et al. reported "The Synthesis of the Antidepressant Fluoxetine". The fluoxetine intermediate 3-methylamino-1 -The preparation method of phenylpropanol, take acetophenone, paraformal...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C215/30C07C213/00
Inventor 杨郭明黄生建陈侠
Owner SHAOXING ZHONGKE BAIYUN CHEM TECH CO LTD
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