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A kind of preparation method of 1-(4-methoxy-benzyl)-2-methyl-octahydroisoquinoline

A technology of octahydroisoquinoline and methyl isoquinoline, applied in the direction of organic chemistry and the like, can solve the problems of complex synthesis, low yield, difficulty in obtaining raw materials, etc., and achieves safe reaction conditions, high yield, and reduced production costs. Effect

Active Publication Date: 2022-03-18
SUZHOU JINGYE MEDICINE & CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Above-mentioned route, acquisition of raw material is difficult, synthesis is complicated, and yield is lower than 30%

Method used

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Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0020] The present invention provides a kind of preparation method of 1-(4-methoxy-benzyl)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline, first 1,2,3,4,5,6,7,8-octahydro-1-(methoxyphenyl)methylisoquinoline is dissolved in a solvent, then add formaldehyde solution, after stirring, then add catalyst, and Introduce hydrogen to carry out catalytic hydrogenation reaction. After the reaction is over, filter out the catalyst and separate by precipitation and distillation to obtain 1-(4-methoxy-benzyl)-2-methyl-1,2,3, 4,5,6,7,8-Octahydroisoquinoline.

[0021] specifically:

[0022] The solvent is methanol, ethanol or isopropanol.

[0023] The formaldehyde solution contains 30%wt formaldehyde.

[0024] The catalyst is Raeburg nickel or palladium carbon.

[0025] The mass ratio of the 1,2,3,4,5,6,7,8-octahydro-1-(methoxyphenyl)methylisoquinoline to the solvent is 1:8-15.

[0026] The molar ratio of the 1,2,3,4,5,6,7,8-octahydro-1-(methoxyphenyl)methylisoquinoline to formaldehyde i...

Embodiment 1

[0032] Put 300g of ethanol into the hydrogenation kettle, add 40g (0.16mol) of 1,2,3,4,5,6,7,8-octahydro-1-(methoxyphenyl)methylisoquinoline, and add it under mechanical stirring 22g (0.22mol) of 30% formaldehyde solution was continuously stirred at 25°C for 4 hours, 6g of Raye's nickel catalyst was added, the hydrogen pressure was 1.8MPa, and stirred at room temperature for 8 hours, the catalyst was removed by filtration, the filtrate was concentrated, separated by vacuum distillation, and 1-( 4-methoxy-benzyl)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline, yield 90%.

Embodiment 2

[0034] Put 800g of ethanol into the hydrogenation kettle, add 80g (0.32mol) of 1,2,3,4,5,6,7,8-octahydro-1-(methoxyphenyl)methylisoquinoline, and add it under mechanical stirring 44g (0.44mol) of 30% formaldehyde solution was continuously stirred at 30°C for 6 hours, 12g of Raye’s nickel catalyst was added, the hydrogen pressure was 1.5MPa, and stirred at room temperature for 8 hours, the catalyst was removed by filtration, the filtrate was concentrated, and vacuum distillation separated to obtain 1-( 4-methoxy-benzyl)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline, yield 90.5%.

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PUM

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Abstract

The invention discloses a preparation method of 1‑(4‑methoxy‑benzyl)‑2‑methyl‑octahydroisoquinoline. First, 1, 2, 3, 4, 5, 6, 7, 8 ‑Octahydro‑1‑(methoxyphenyl)methylisoquinoline is dissolved in the solvent, then add formaldehyde solution, after stirring, then add the catalyst, and feed hydrogen to carry out the catalytic hydrogenation reaction, after the reaction, filter out Catalyst, and separated by precipitation and distillation to obtain 1-(4-methoxy-benzyl)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline . The method of the invention has the characteristics of mild and safe reaction conditions, green environmental protection, reduced side reactions, high yield, good purity, simple and convenient operation, etc., which enables the preparation industry to achieve green environmental protection, safety and high efficiency, and simultaneously reduces production costs.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a 1-(4-methoxy-benzyl)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinone The preparation method of phenoline. Background technique [0002] 1-(4-methoxy-benzyl)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline, molecular formula: C 18 h 25 NO, CAS number: 31414-58-1. [0003] 1-(4-methoxy-benzyl)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline is a key intermediate in the synthesis of dextromethorphan. Dextromethorphan, also known as dextromethorphan hydrobromide, English abbreviation DM or DXM, is an antitussive drug, chemical name (+)-cis-1,3,4,9,10,10a- Hexahydro-6-methoxy-11-methyl-2H-10,4a-iminoethanophenanthrene is a central antitussive drug, mainly used for dry cough. It is suitable for coughs caused by colds, acute or chronic bronchitis, bronchial asthma, pharyngitis, tuberculosis, and other upper respiratory tract infections. [0004] 1-(4-methoxy-benzyl)-2-methyl-1...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D217/20
CPCC07D217/20
Inventor 沈建伟
Owner SUZHOU JINGYE MEDICINE & CHEM
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