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Method for preparing dextroa-[2-(naphthoxy, ethyl] phenyl methylamine derivatives

A technology of naphthyloxy and benzylamine, which is applied in the field of preparation of dextrorotatory α-[2-ethyl]benzylamine derivatives, can solve problems such as poor therapeutic effect, unsafe users, and vomiting, and reduce Product cost and the effect of saving the amount of raw materials

Inactive Publication Date: 2005-12-21
曹丽 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] According to research, the dosage of dapoxetine for treating premature ejaculation is 60mg, if the dosage is less than 60mg, the therapeutic effect will be poor, and when the dosage reaches 100mg, more than 90% of people will experience side effects such as vomiting
Since only the dextrorotatory form of dapoxetine is effective in treating premature ejaculation, and the levorotatory form is ineffective, if the mixed form is used to treat premature ejaculation, the dosage should reach 120mg, which is unsafe for users, so clinical practice Dapoxetine medley cannot be used in the treatment of premature ejaculation

Method used

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  • Method for preparing dextroa-[2-(naphthoxy, ethyl] phenyl methylamine derivatives
  • Method for preparing dextroa-[2-(naphthoxy, ethyl] phenyl methylamine derivatives
  • Method for preparing dextroa-[2-(naphthoxy, ethyl] phenyl methylamine derivatives

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Effect test

Embodiment 1

[0047] S-(+)N, the preparation of N-dimethyl-α-[2-(naphthyloxy) ethyl] benzylamine hydrochloride:

[0048] 1. Preparation of β-aminophenylpropionic acid

[0049] Add 13g of benzaldehyde, 14g of malonic acid and 7g of ammonium acetate into a 250ml three-necked bottle filled with 150ml of DMF at one time, and reflux at 122°C for 8 hours under stirring. After the reaction was finished, add 1.5 g of active carbon and filter while hot, and the filtrate was evaporated to dryness under a pressure of 720 mmHg. Add 100ml each of chloroform and 10% aqueous sodium bicarbonate solution to the evaporated matter, stir vigorously for half an hour, and separate the water layer at rest, then add 100ml aqueous sodium bicarbonate solution to the organic layer to wash, combine the aqueous layers separated for the second time, and add 15% hydrochloric acid dropwise solution, adjust the pH of the solution to 3-4, filter and dry the precipitate to obtain 12.2 g of β-aminophenylpropionic acid, with ...

Embodiment 2

[0068] S-(+)N, the preparation of N-diethyl-α-[2-(naphthyloxy)ethyl]benzylamine hydrochloride:

[0069] 1. Preparation of β-aminophenylpropionic acid

[0070] Add 13g of benzaldehyde, 14.2g of malonic acid and 7.5g of ammonium acetate into a 250ml three-necked flask filled with 150ml of DMF at one time, and react under reflux at 115°C for 5 hours while stirring. After the reaction was finished, add 1.5 g of active carbon and filter while hot, and the filtrate was evaporated to dryness under a pressure of 720 mmHg. Add 150ml each of chloroform and 10% aqueous sodium bicarbonate solution to the evaporated matter, stir vigorously for half an hour, separate the water layer at rest, add 100ml aqueous sodium bicarbonate solution to the organic layer to wash, combine the aqueous layers separated for the second time, and add 15% hydrochloric acid dropwise solution, adjust the pH of the solution to 3-4, filter and dry the precipitate to obtain 11.5 g of β-aminophenylpropionic acid, wi...

Embodiment 3

[0089] S-(+)N, the preparation of N-dimethyl-α-[2-(naphthyloxy) ethyl] benzylamine sulfate:

[0090] 1. Preparation of β-aminophenylpropionic acid

[0091]Add 13g of benzaldehyde, 14g of malonic acid and 14g of ammonium acetate into a 250ml three-necked bottle filled with 150ml of benzene at one time, and react at 62°C for 5 hours under stirring. After the reaction was finished, add 1.5 g of active carbon and filter while hot, and the filtrate was evaporated to dryness under a pressure of 720 mmHg. Add 100ml each of chloroform and 10% aqueous sodium bicarbonate solution to the evaporated matter, stir vigorously for half an hour, and separate the water layer at rest, then add 100ml aqueous sodium bicarbonate solution to the organic layer to wash, combine the aqueous layers separated for the second time, and add 15% hydrochloric acid dropwise solution, adjust the pH of the solution to 3-4, filter and dry the precipitate to obtain 12.3 g of β-aminophenylpropionic acid, with a me...

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Abstract

This invention involves a synthesis method for dextrorotatory alpha- [2-(naphthoxy) ethyl] toluidine derivatives, including: make benzaldehyde react with malonic acid and ammonium acetate, then split it with dextrorotatory anhydrous tartaric to get dextrorotatory beta-aminophenylpropionic acid, after alkyl substitution and deoxidizing to alcohol, react with alpha-bromonaphthalene. This invention has saved the raw materials consumption that every step reacts afterwards, the castoff is reduced greatly, thus reduced the cost.

Description

Technical field [0001] The invention relates to a method for preparing dextrorotatory α-[2-(naphthyloxy)ethyl]benzylamine derivatives and their pharmaceutically acceptable salts. Background technique [0002] It has been noted that the intake of monoamines is closely related to various diseases and symptoms, for example, fluoxetine hydrochloride is a selective serotonin uptake inhibitor used in the treatment of depression, eating disorders, alcoholism and other disorders. [0003] Dapoxetine (Dapoxetine), chemical name N, N-dimethyl-α-[2-(naphthyloxy) ethyl] benzylamine hydrochloride (N, N-dimethyl-α-[2-( Naphthalenyloxy)ethyl]benyenemethanaminehydrochloride), is a selective serotonin uptake inhibitor, which can be used to treat depression, alcoholism, weight loss, amnesia, etc. It is effective for forgetfulness, irritability, depression, and withdrawn. An oral medication used to treat premature ejaculation in men. The drug is a selective serotonin uptake inhibitor and ha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/56
Inventor 陈品岗曹丽陈天度
Owner 曹丽
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