Process for preparing optically pure N-methyl-3-phenyl-3-hydoxypropylamine

A technology of hydroxypropylamine and methyl, which is applied in the field of preparation of optically pure N-methyl-3-phenyl-3-hydroxypropylamine, achieving the effects of high yield, high resolution efficiency, and simple and easy process

Inactive Publication Date: 2007-05-09
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

According to research, some patients have side effects such as anxiety and talking to themselves after taking fluoxetine.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Weigh 3g of N-methyl-3-phenyl-3-hydroxypropylamine and 3.27g of dibenzoyl-L-tartaric acid into a 100ml round bottom flask, add 10ml of methanol and stir at room temperature. The crystals gradually dissolved and the solution became transparent. Add acetone until the solution just becomes cloudy, then add a small amount of methanol until the solution becomes clear again. Stir for two days, filter, and dry under an infrared lamp to obtain 3.07 g of white powdery crystals-2,3-dibenzoyl-L-tartaric acid-bis[methyl(1R-1-phenyl-1-hydroxy)propyl ] Ammonium salt. Resolution yield is 48.99%. Optical rotation: -46.0 (C=1, CH 3 OH).

[0024] Weigh 3g of 2,3-dibenzoyl-L-tartaric acid-bis[methyl(1R-1-phenyl-1-hydroxy)propyl]ammonium salt into a 100ml round bottom flask, add 3ml of water , 6ml of ethyl acetate, 0.5ml of concentrated sulfuric acid, stirred for 2hr. Then transfer to a separatory funnel. The upper organic phase was evaporated to dryness to obtain dibenzoyl-L-tartari...

Embodiment 2

[0027] Weigh 3g of N-methyl-3-phenyl-3-hydroxypropylamine and 3.27g of bromocamphoric acid into a 100ml round bottom flask, add 10ml of methanol and stir at room temperature. The crystals gradually dissolved and the solution became transparent. Add acetone until the solution just becomes cloudy, then add a small amount of methanol until the solution becomes clear again. Stir for two days, filter, and dry with an infrared lamp to obtain 2.57 g of white powdery crystals. Resolution yield is 40.98%. Optical rotation: -44.6 (C=1, CH 3 OH).

[0028] Recrystallize the above-mentioned salt crystals with alcohol, then weigh 3g of the salt and put it into a 100ml round bottom flask, add 3ml of water, 6ml of ethyl acetate, and 0.5ml of concentrated sulfuric acid, and stir for 2hr. Then transfer to a separatory funnel. The upper organic phase was evaporated to dryness to obtain bromocamphoric acid. 0.28 g of calcium oxide and 0.1 g of calcium carbonate were added to the lower aqueou...

Embodiment 3

[0031] Weigh 3g of N-methyl-3-phenyl-3-hydroxypropylamine and 3.27g of hydroxyphenylglycine into a 100ml round bottom flask, add 10ml of methanol and stir at room temperature. The crystals gradually dissolved and the solution became transparent. Add acetone until the solution just becomes cloudy, then add a small amount of methanol until the solution becomes clear again. Stir for two days, filter, and dry with an infrared lamp to obtain 2.29 g of white powdery crystals. Resolution yield is 36.5%. Optical rotation: -42.1 (C=1, CH 3 OH).

[0032]Weigh 3g of salt into a 100ml round bottom flask, add 3ml of water, 6ml of ethyl acetate, 0.5ml of concentrated sulfuric acid, and stir for 2hr. Then transfer to a separatory funnel. The upper organic phase was evaporated to dryness to obtain hydroxyphenylglycine. 0.28 g of calcium oxide and 0.1 g of calcium carbonate were added to the lower aqueous phase, and stirred for 4 hr until pH = 7-8. The calcium sulfate precipitate was rem...

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Abstract

A process for preparing optically-pure N-methyl-3-phenyl-3-hydroxypropylamine includes converting the racemate of N-methyl-3-phenyl-3-hydroxypropylamine by optically pure diphenyl formacyl tartaric acid or bromocamphoric acid or hydroxyphenyl glycine to obtain diastereoisomeric salt, separating and acidifying. Its advantages are short period and high efficiency.

Description

technical field [0001] The invention relates to a preparation method of optically pure N-methyl-3-phenyl-3-hydroxypropylamine. Background technique [0002] N-methyl-3-phenyl-3-hydroxypropylamine is a light yellow crystalline powder, insoluble in water, easily soluble in methanol, chloroform, or n-hexane. The melting point is 60-61°C. [0003] N-methyl-3-phenyl-3-hydroxypropylamine is an intermediate of a bicyclic antidepressant drug fluoxetine newly listed in the United States. Fluoxetine is different from tricyclic antidepressants in terms of structure and pharmacological effects. Fluoxetine and its metabolite norfluoxetine are selective and competitive to neurotransmitters, and jointly inhibit the reabsorption of serotonin by nerve cells, and have few other pharmacological effects, so they have fewer side effects and have become Promising antidepressant drug. [0004] Fluoxetine has two types of isomers, R and S, which can be obtained through the corresponding interme...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C215/30C07C213/10
Inventor 胡先明龚晓艳邱国福何建社
Owner WUHAN UNIV
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