Process for synthesizing duloxetine hydrochloride

A technology of duloxetine hydrochloride and synthesis process, applied in organic chemistry and other directions, can solve the problems of chiral resolution, incomplete dissolution of raw materials, incomplete reduction, etc., and achieve the effect of overcoming low optical purity

Inactive Publication Date: 2011-05-25
王念军
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Problems solved by technology

[0003] The existing synthesis process has the key problem of incomplete dissolution of raw materials and incomplete reduction, so that the next step of chiral resolution cannot be carried out, so the inventor intends to improve the existing synthesis process

Method used

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Embodiment Construction

[0016] The synthesis process comprises the following steps:

[0017] 1. Preparation of 2-thiophene-2-dimethylamine methyl ethyl ketone hydrochloride: In a 10L three-necked flask, add 6.56mol (715ml) of 2-acetylthiophene and 8.26mol (674g) of dimethylamine hydrochloride , paraformaldehyde 9.26mol (293g), concentrated hydrochloric acid 65ml and isopropanol 2900ml, heated, stirred and refluxed, a large amount of white solids precipitated after 1h, and the reaction stopped after 6h.

[0018] The complete reaction of the raw material was monitored by TLC, Rf=0.66 (n-hexane:ethyl acetate=5:1) and the reaction liquid was cooled, the solid was collected by filtration, washed with 250ml×3 ethanol, and the white solid was vacuum-dried for 16h to obtain 1380g of white crystals . Yield 95.3%, mp: 188.3°C-190.2°C.

[0019] 2. Preparation of N, N-dimethyl-3-hydroxy-3-(2-thiophene)-propylamine: In a 10L three-necked flask, add the 2-thiophene-2-dimethylaminomethyl ethyl ketone salt obtaine...

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Abstract

The invention belongs to the field of medicine synthesis, relates to a process for synthesizing duloxetine hydrochloride, and solves the technical problem to provide a new process for synthesizing the duloxetine hydrochloride, which makes raw materials dissolved completely and reduced thoroughly. The synthetic process comprises the following steps of: 1, preparing 2-thienyl-2-dimethylaminomethyl butanone hydrochloride; 2, preparing N,N-dimethyl-3-hydroxy-3-(2-thienyl)propanamine; 3, preparing (S)-N,N-dimethyl-3-hydroxy-3-(2-thienyl)propanamine; 4, preparing (S)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine; 5, preparing (S)-N-methyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine; and 6, preparing (S)-N-methyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine hydrochloride. By the six steps of the process, the total synthetic yield is 24.1 percent.

Description

technical field [0001] The invention belongs to the field of drug synthesis, in particular to a synthesis process of duloxetine hydrochloride. Background technique [0002] Duloxetine hydrochloride, the chemical name is (S)-N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)-1-propanamine hydrochloride, is a kind of 5- Cymbalta is an antidepressant with dual inhibition of serotonin and norepinephrine reuptake. In September 2002, it was approved by the US FDA to treat severe depression, and its hydrochloride was used clinically. In September 2004, the US FDA approved a supplementary indication for the treatment of diabetic extrinsic nerve pain. [0003] The existing synthesis process has the key problems of incomplete dissolution of raw materials and incomplete reduction, so that the next step of chiral resolution cannot be performed. Therefore, the inventor intends to improve the existing synthesis process. Contents of the invention [0004] The technical problem to be solved by t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/20
Inventor 王念军
Owner 王念军
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