N-alkyl-N-[2-hydroxy-3-(aryloxy)propanyl]-2-(arylsulfonyl)benzylamine and preparation method and application

A technology based on methoxyphenylthio and propyl groups, which is applied in the preparation of sulfides, organic chemistry, etc., can solve the problems of hysteresis, nausea, anxiety, insomnia, urgent research, etc., and achieve easy operation and simple preparation process Effect

A technology based on methoxyphenylthio and propyl groups, which is applied in the preparation of sulfides, organic chemistry, etc., can solve the problems of hysteresis, nausea, anxiety, insomnia, urgent research, etc., and achieve easy operation and simple preparation process Effect

CN1724515AInactive Publication Date: 2006-01-25TIANJIN UNIV
0 Cites 2 Cited by

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • N-alkyl-N-[2-hydroxy-3-(aryloxy)propanyl]-2-(arylsulfonyl)benzylamine and preparation method and application
  • N-alkyl-N-[2-hydroxy-3-(aryloxy)propanyl]-2-(arylsulfonyl)benzylamine and preparation method and application
  • N-alkyl-N-[2-hydroxy-3-(aryloxy)propanyl]-2-(arylsulfonyl)benzylamine and preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 3-(2-Trifluoromethylphenoxy)propylene oxide

[0026] Epichlorohydrin (1.59g, 0.017mol), tetrabutylammonium bromide (0.05g, 0.00017mol), potassium carbonate (1.1886g, 0.0086mol) in water (40mL) solution, o-trifluoromethylphenol ( 0.5582g, 0.0034mol) into the reaction bottle, and reacted at room temperature for 24h. Extracted with dichloromethane (30mL×3), washed with 3% NaOH alkali (50mL×3), washed with water (50mL×3), dried (anhydrous sodium sulfate), and evaporated to remove the solvent under reduced pressure to obtain a light yellow oil (0.5164g , 68.74%).

[0027] N-methyl-N-[2-hydroxy-3-(2-trifluoromethylphenoxy)propanyl]-2-(2-methoxyphenylthio)benzylamine

[0028] N-methyl-2-(arylthio)benzylamine (0.4g, 0.00155mol), 3-(2-trifluoromethylphenoxy)propylene oxide (0.5164g, 0.00237mol), absolute ethanol 50mL was put into a reaction flask, and heated to reflux at 84°C for 24h. After cooling, the solvent was distilled off under reduced pressure to obtain a light yello...

Embodiment 2

[0031] 3-(4-Chlorophenoxy)epoxide

[0032] Epichlorohydrin (1.59g, 0.017mol), tetrabutylammonium bromide (0.05g, 0.00017mol), potassium carbonate solution (1.1886g, 0.0086mol) in water (40mL) solution, p-chlorophenol (0.4429g , 0.0034mol) into the reaction flask, and reacted at room temperature for 24h. Dichloromethane extraction (30mL × 3), 3% NaOH alkali washing (50mL × 3), water washing (50mL × 3), drying (anhydrous sodium sulfate), decompression to remove the solvent, to obtain a light yellow oil (0.6153g , 96.76%).

[0033] N-Methyl-N-[2-hydroxy-3-(4-chlorophenoxy)propanyl]-2-(2-methoxyphenylthio)benzylamine

[0034] Put N-methyl-2-(arylthio)benzylamine (0.4g, 0.00155mol), 3-(4-chlorophenoxy)propylene oxide (0.6153g, 0.00333mol), and 50mL of absolute ethanol into In the reaction flask, heat to reflux at 84°C for 24h. After cooling, the solvent was distilled off under reduced pressure to obtain a light yellow gum, which was separated by PTLC (ethyl acetate:petroleum et...

Embodiment 3

[0037] 3-(2-Chlorophenoxy)propylene oxide

[0038]Epichlorohydrin (1.59g, 0.017mol), tetrabutylammonium bromide (0.05g, 0.00017mol), potassium carbonate solution (1.1886g, 0.0086mol) in water (40mL), o-chlorophenol (0.4429g , 0.0034mol) into the reaction flask, and reacted at room temperature for 24h. Extracted with dichloromethane (30mL×3), washed with 3% NaOH alkali (50mL×3), washed with water (50mL×3), dried (anhydrous sodium sulfate), and evaporated the solvent under reduced pressure to obtain a colorless oil (0.6530, 76.1%).

[0039] N-Methyl-N-[2-hydroxy-3-(2-chlorophenoxy)propanyl]-2-(2-methoxyphenylthio)benzylamine

[0040] Put N-methyl-2-(arylthio)benzylamine (0.4g, 0.00155mol), 3-(2-chlorophenoxy)propylene oxide (0.8586g, 0.00465mol), and 50mL of absolute ethanol into In the reaction flask, heat to reflux at 84°C for 24h. After cooling, the solvent was distilled off under reduced pressure to obtain a light yellow gum, which was separated by PTLC (ethyl acetate:pe...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses the structure of N-alkyl-N-[2-hydroxyl-3-(aryloxy) propalkyl]-2-(arylthioyl) benzylamine with anti-depression activity, its preparing process and use, wherein the preparing process comprises reacting 1 mol of aryl phenol with 1-10 mol of epioxychloropropane in 1-5 mol aqueous solution of potassium carbonate or sodium carbonate at the presence of tetra butyl ammonium bromide for 12-48 hours under room temperature, thus obtaining 3-aryloxy epioxypropane, then subjecting 1 mol of N-alkyl-2-(arylthioyl) benzylamine and 1-5 mol of 3-aryloxy epioxypropane to backflow reaction for 5-48 hours in anhydrous alcohol or absolute methanol. The compounds can be in existence by the form of free alkali or salt for preparing medicaments for resisting depression. The advantages of the invention include simple preparing process and easy operation.

Description

technical field [0001] The present invention relates to a structure of N-alkyl-N-[2-hydroxyl-3-(aryloxy)propanyl]-2-(arylthio)benzylamine with antidepressant activity, its preparation method and application , the technology belongs to the field of medicinal chemistry. Background technique [0002] Depression is a common mental illness, which is an emotional disorder. As the pace of life continues to accelerate, people's mental pressure is gradually increasing. Depression has become a common disease in modern society, with a high incidence, and its incidence is rising rapidly. : According to incomplete statistics, at present the world's depression patients have accounted for 3%-5% of the world's population, almost seen in all ages, and its prevalence is about 3% in the general population, and the patient population in general hospital health services In patients with chronic physical diseases (such as cardiovascular disease, diabetes), the rate of depressive disorder can be ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
25 Jan 2006
Publication
CN1724515A
IPC
C07C323/31; C07C319/20
Inventors
李爱军; 刘东志