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Preparation method of N,N-dimethyl-3-hydroxy-3-aryl propyl amine

A dimethylformamide and dimethyl technology, applied in the N field, can solve the problems of low Mannich reaction yield, complicated operation, long reaction time, etc., and achieve the effects of easy industrial production, simple preparation process, and short reaction time.

Inactive Publication Date: 2007-03-14
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the above-mentioned preparation method has shortcomings such as low Mannich reaction yield, long reaction time, complicated operation, etc., so the synthesis research of this type of intermediate is extremely important

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Add 2-acetylthiophene (50.5g, 0.4mol), DMFDMA (95.2g, 0.8mol) and N,N-dimethylformamide (250ml) into the reaction flask, heat up to 100°C for 3 hours, and distill out under reduced pressure The solvent was cooled to obtain yellow crystals, which were recrystallized from ethyl acetate (400ml) to obtain light yellow crystals of N,N-dimethyl-3-oxo-3-(2-thienyl)propenylamine (67.4g, 92.1%) . mp.117~119℃. MS m / z: 180.9, 148.0, 110.9, 98.0, 55.0, 42.0.

Embodiment 2

[0018] Lithium aluminum hydride (38g, 1.0mol) and tetrahydrofuran (300ml) were added into the reaction flask, and N,N-dimethyl-3-oxo-3-(2-thienyl)propenylamine (36.2g, 0.2 mol), after adding, react at room temperature for 10 hours, under cooling, slowly add water (200ml), continue to stir for 30 minutes, filter, extract the filtrate with dichloromethane (100ml×3), dry, filter, evaporate the solvent to obtain light yellow Viscous oily N,N-dimethyl-3-hydroxy-3-(2-thienyl)propylamine (33.5 g, 82.4%) solidified upon cooling to give a white solid, mp.70-73°C. MS m / z: 185.1, 113.0, 85.0, 58.1, 30.1.

Embodiment 3

[0020] Add acetophenone (60.0, 0.5), DMFDMA (119g, 1.0mol) and N,N-dimethylformamide (300ml) into the reaction flask, heat up to 100°C for 4 hours, evaporate the solvent under reduced pressure and cool to obtain a yellow It was crystallized and recrystallized from ethyl acetate (450ml) to give pale yellow crystals of N,N-dimethyl-3-oxo-3-phenylpropenylamine (78.9g, 90.1%). mp.93~94℃. MS m / z: 175.0, 158.0, 131.0, 98.0, 77.0, 42.0.

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PUM

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Abstract

The present invention discloses a preparation method of N,N-dimethyl-3-hydroxy-3-arylpropylamine. Said method includes the following steps: adding phenyl methyl ketone or 2-acetyl thiophenol and N,N-dimethylformamide dimethyl acetal into solvent including benzene and N,N-dimethylformamide, after the reaction is completed, evaporating solvent, cooling to obtain yellow crystal product, using solvent of ethyl acetate, etc, to make recrystallization and obtain N,N-dimethyl-3-oxo-3-aryl propyleneamine; adopting lithium aluminium hydride as reducing agent, adding N,N-dimethyl-3-oxo-3-aryl propyleneamine and reducing agent into the solvents of benzene, etc., making reaction to obtain product; or adopting sodium borohydride as reducing agent, adding N,N-dimethyl-3-oxo-3-aryl propyleneamine and reducing agent into solvents of acetic acid, etc., making reaction to obtain product; making said product undergo the process of phase separation, evaporating the organic phase obtained by means of phase separation so as to obtain N,N-dimethyl-3-hydrox-3-arylpropylamine.

Description

technical field [0001] The invention relates to a preparation method of N,N-dimethyl-3-hydroxy-3-arylpropylamine, which belongs to the preparation technology of important intermediates of various antidepressants. Background technique [0002] N, N-dimethyl-3-hydroxy-3-arylpropylamine compounds are important pharmaceutical intermediates, which can be used to synthesize fluoxetine hydrochloride, atomoxetine hydrochloride, duloxetine hydrochloride and other drugs. Such drugs have been widely used in the treatment of depression and are commonly used throughout the world. Therefore a large number of literatures have reported the synthetic method about this kind of intermediate. [0003] N, N-dimethyl-3-hydroxyl-3-arylpropylamines examples of known preparation methods include: in many patents [US 4314081, US 4194009, and EP 529842 etc.] described the preparation of fluoxetine hydrochloride Synthetic, the important intermediate is N, N-dimethyl-3-hydroxyl-3-phenylpropylamine, it ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/70C07C211/27C07D333/20
Inventor 李爱军刘东志周雪琴王健
Owner TIANJIN UNIV