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Preparation of N,N-dimethyl-1-phenyl-3-(1-naphthoxy) propanamine

A preparation process, naphthyloxy technology, applied in the field of N, can solve the problems of long synthetic route, difficult to control the source or by-product, not a synthetic method, etc., and achieve the effect of short synthetic route

Inactive Publication Date: 2009-02-18
TAIZHOU VOCATIONAL & TECHN COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0022] Among these routes, the synthetic routes adopted are relatively long, and there are problems such as highly toxic and explosive raw materials, sources or by-products that are difficult to control, and are not an ideal synthetic method, which needs further improvement

Method used

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  • Preparation of N,N-dimethyl-1-phenyl-3-(1-naphthoxy) propanamine
  • Preparation of N,N-dimethyl-1-phenyl-3-(1-naphthoxy) propanamine
  • Preparation of N,N-dimethyl-1-phenyl-3-(1-naphthoxy) propanamine

Examples

Experimental program
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Effect test

Embodiment 1

[0036] 3-(1-Naphthyloxy)-1-propiophenone

[0037] Dissolve 10g (0.178mol) of potassium hydroxide in N-dimethylformamide (DMF) for 150min, add 25g (0.174mol) of 1-naphthol, react at room temperature for 1h, then add 25g (0.148mol) of 3 -Chloro-1-propiophenone, reflux for 10 h, add water, extract with ethyl acetate, and concentrate to obtain 31.9 g of brown oil (unpurified, crude yield 78.1%).

Embodiment 2

[0039] N-Methyl-1-phenyl-3-(1-naphthyloxy)propylamine

[0040] 60ml of methanol, 60ml of 40% methanol solution of methylamine and 5g (0.018mol) of crude 3-(1-naphthyloxy)-1-propiophenone were sequentially added, and the mixture was refluxed for 5h. Concentrate, add 100ml of water, extract with dichloromethane, concentrate, dissolve the concentrate in 300ml of methanol, add 1g (0.027mol) NaBH at 0°C 4 , reacted for 1 h, concentrated, added water, extracted with dichloromethane, and evaporated the solvent to obtain 4.3 g of dark viscous material (unpurified, crude product yield 82.1%).

Embodiment 3

[0042] N,N-Dimethyl-1-phenyl-3-(1-naphthyloxy)propylamine

[0043] Add 4ml (0.067mol) of glacial acetic acid, 4.3g (0.015mol) of crude N-methyl-1-phenyl-3-(1-naphthyloxy)propylamine, 60ml of methanol, 7ml (0.086mol) of 37 % formaldehyde, 1.5g (0.024mol) NaBH 3 CN, react at room temperature for 1h. Concentrate, add water, extract with dichloromethane, evaporate the solvent to obtain 4 g of yellow viscous substance (yield 88.6%).

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Abstract

The present invention provides a preparation technology of N, N-dimethyl-1-benzyl-3-(1-naphthyloxies) propylamine, and belongs to the technical field of medical and chemical industry. The present invention solves the problems that the prior synthesis route is long, and the high toxicity, explosiveness, sources or byproducts of raw materials are hard to control. In the preparation technology of the N, N-dimethyl-1-benzyl-3-(1-naphthyloxies) propylamine, 3-chlorine-1-phenyl propanone is used as a starting raw material and is condensed with 1-naphthol, and the N, N-dimethyl-1-benzyl-3-(1-naphthyloxies) propylamine can be prepared through amination, reduction and methylation. The present invention has the advantages that the synthesis route is shortened, and the cost is reduced.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical industry, and relates to a preparation process of N,N-dimethyl-1-phenyl-3-(1-naphthyloxy)propylamine. Background technique [0002] N,N-Dimethyl-1-phenyl-3-(1-naphthyloxy)propylamine is a selective serotonin reuptake inhibitor (SSRI) -- the API of dapoxetine , the drug is widely used to treat depression and related affective disorders. It is currently being used in clinical research for the treatment of premature ejaculation in men. [0003] About N, the preparation of N-dimethyl-1-phenyl-3-(1-naphthyloxy) propylamine, existing method reports as follows: [0004] Known information: [0005] European patent Ep0288188; Chinese patent CN88102018A [0006] 1. Using 3-phenylpropanol as raw material, chlorination by thionyl chloride, etherification with 1-naphthol, bromination of NBS, amination of dimethylamine to obtain the target product or hydrogenation after reaction with sodium az...

Claims

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Application Information

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IPC IPC(8): C07C215/28C07C213/02C07C213/00
Inventor 蒋军荣
Owner TAIZHOU VOCATIONAL & TECHN COLLEGE
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