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Process for preparation of 3-(2-hydroxy-5-methylphenyl)-n,n-diisopropyl-3phenylpropylamine

A technology of methylphenyl and diisopropyl, applied in the field of organic chemistry, can solve problems such as short time and low price

Inactive Publication Date: 2011-11-02
LEK PHARMA D D
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although several processes for the preparation of 3-(2-hydroxy-5-methylphenyl)-N,N-diisopropyl-3-phenylpropylamine have been described, they still require less time, are less expensive and are A more industrially applicable method under mild conditions

Method used

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  • Process for preparation of 3-(2-hydroxy-5-methylphenyl)-n,n-diisopropyl-3phenylpropylamine
  • Process for preparation of 3-(2-hydroxy-5-methylphenyl)-n,n-diisopropyl-3phenylpropylamine
  • Process for preparation of 3-(2-hydroxy-5-methylphenyl)-n,n-diisopropyl-3phenylpropylamine

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Embodiment Construction

[0044] The method of the present invention is described with flow chart, and it comprises the following steps:

[0045] a) reducing the lactone ring of the optionally substituted compound of formula I to open the lactone ring to obtain a compound 2-hydroxyphenylpropanol derivative represented by formula II, which may be optionally substituted, preferably 3, 4-Dihydro-6-methyl-4-phenyl-2-benzopyran-2-one reduces the lactone ring opening to give 3-(2-hydroxy-5-methylphenyl)-3- Phenylpropanol;

[0046] b) Conversion of the two hydroxyl groups of the compound of formula II using the same reagent to form a di-O-substituted derivative by treatment with a reagent that simultaneously activates the alcohol moiety and protects the phenol moiety. Said transformation is characterized in that -O- substituents on the propyl chain react more readily with diisopropylamine than -O-substituents on the aromatic rings to give optionally substituted compounds of formula III;

[0047] c) using ha...

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Abstract

A new process for preparation of 3-(2-hydroxy-5-methylphenyl)-N,N-diisopropyl-3-phenylpropylamine from 3,4-dihydro-6-methyl-4-phenyl-2-benzopyran-2-one is characterized by intermediates such as 3-(2-hydroxy-5-methyl phenyl)-3- phenylpropanol and its sulphonated derivatives and amination in presence of sodium iodide.

Description

technical field [0001] The invention belongs to the field of organic chemistry and relates to a novel and effective synthetic method for preparing 3-(2-hydroxyl-5-methylphenyl)-N,N-diisopropyl-3-phenylpropylamine, which is characterized in The key intermediate lies in the readily available 3-(2-hydroxy-5-methylphenyl)-3-phenylpropanol. Background technique [0002] Several synthetic methods for the preparation of 3-(2-hydroxy-5-methylphenyl)-N,N-diisopropyl-3-phenylpropylamine have been disclosed. The prior art describes the preparation of racemic and enantiomerically pure products obtained either by resolution of the enantiomers in a final step or by chiral synthesis. [0003] EP325571 discloses a multi-step process for the preparation of 3-(2-hydroxy-5-methylphenyl)-N,N-diisopropyl-3-phenylpropylamine from 4-(-methoxy -5-methylphenyl)-6-methyl-3,4-chromanone as the first intermediate. Opening of the lactone ring in an alkaline medium with simultaneous esterification of ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/68C07C309/65C07C309/72
CPCC07C309/73C07C213/02C07C309/65C07C215/54
Inventor R·托普拉克
Owner LEK PHARMA D D
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