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Preparation method of paroxetine hydrochloride and intermediate thereof

A technology of paroxetine hydrochloride and ethyl acetate, which is applied in the refining field of paroxetine hydrochloride, can solve the problems of small amount of recrystallization solvent, fast crystallization, loss and the like, and achieves a product with good product purity, strong controllability and simple operation. Effect

Inactive Publication Date: 2009-10-21
万全万特制药江苏有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This technology has several advantages over existing methods: it can be operated with ease at an affordable price; produces products that are very pure but have poor quality; there's no expensive equipment needed or complicated processes involved during manufacturing process.

Problems solved by technology

This patented technical problem addressed in this patent relates to finding efficient ways to produce chemically pure substances called parafexidone or perpendicularisporphyrimidone HCl(PFI)). Current methods involve complicated processes like extractions into different materials followed by multiple steps before being converted into desired products. There have been attempts made towards improving these techniques but they still suffer drawbacks such listed below.

Method used

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  • Preparation method of paroxetine hydrochloride and intermediate thereof
  • Preparation method of paroxetine hydrochloride and intermediate thereof
  • Preparation method of paroxetine hydrochloride and intermediate thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Under nitrogen protection, 1500 g of N-methylparoxetine, 12.99 kg of toluene (C.P.), and 525 g of triethylamine (C.P.) were added to a 20 L reactor. The temperature was controlled at about 10°C, and 2055 g of phenyl chloroformate was slowly added dropwise to the system. After the dropwise addition, the reaction was refluxed for 2h. Remove from heat and let cool. Suction filtration, the filter cake was rinsed with 0.25kg toluene. The solvent was distilled off under reduced pressure. Add 6.54kg of petroleum ether and stir for 1h. Suction filtration, the filter cake was dried in a blast drying oven at 50°C for 6 hours to obtain 1904g (-)-trans-4R-(4-fluorophenyl)-3S-{[3′,4′-(methylenebis Oxy)phenoxy]methyl}-1-phenoxycarbonylpiperidine, yield 97%, TLC showed a single point.

Embodiment 2

[0022] Under nitrogen protection, 1500 g of N-methylparoxetine, 19.485 kg of toluene (C.P.), and 525 g of triethylamine (C.P.) were added to a 20 L reactor. The temperature was controlled at about 10°C, and 2055 g of phenyl chloroformate was slowly added dropwise to the system. After the dropwise addition, the reaction was refluxed for 2h. Remove from heat and let cool. Suction filtration, the filter cake was rinsed with 0.25kg toluene. The solvent was distilled off under reduced pressure. Add 6.54kg of methanol and stir for 1h. Suction filtration, the filter cake was dried in a blast drying oven at 50°C for 6 hours to obtain 1879g (-)-trans-4R-(4-fluorophenyl)-3S-{[3′,4′-(methylenebis Oxy)phenoxy]methyl}-1-phenoxycarbonylpiperidine, yield 96%, TLC showed a single point.

Embodiment 3

[0024] Under nitrogen protection, 1500 g of N-methylparoxetine, 15 L of dichloromethane (C.P.), and 525 g of triethylamine (C.P.) were added to a 20 L reactor. The temperature was controlled at about 10°C, and 2055 g of phenyl chloroformate was slowly added dropwise to the system. After the dropwise addition, the reaction was refluxed for 2h. Remove from heat and let cool. Suction filtration, filter cake rinse with 250ml toluene. The solvent was distilled off under reduced pressure. Add 6.54kg of methanol and stir for 1h. Suction filtration, the filter cake was dried in a blast drying oven at 50°C for 6h to obtain 1845g (-)-trans-4R-(4-fluorophenyl)-3S-{[3′,4′-(methylenebis Oxy)phenoxy]methyl}-1-phenoxycarbonylpiperidine, yield 94%, TLC showed a single point.

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Abstract

The invention relates to a preparation method of an important intermediate of paroxetine hydrochloride for resisting various kinds of depression, which is suitable for industrial production, wherein the formula of the intermediate is shown in formula (1): compound (-)-trans-4R-(4- fluorophenyl)-3S-{[3', 4'-(methylene dioxygen group) phenoxyl] methyl}-1-phenoxy hydroxypiperidine. The invention also relates to a method for finely preparing paroxetine hydrochloride.

Description

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Claims

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Application Information

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Owner 万全万特制药江苏有限公司
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