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Process for the dehydration of substituted 4-dimethylamino-2-aryl-butan-2-ol compounds and process for the preparation of substituted dimethyl-(3-aryl-butyl)- amine compounds by heterogeneous catalysis

a technology of arylbutan and dimethylamino-2-ol, which is applied in the field of process for the dehydration of substituted 4dimethylamino2arylbutan2ol compounds and to the process for the preparation of substituted dimethyl(3arylbutyl)amine compounds by heterogeneous catalysis, can solve the problems of equipment corrosion, acid used for the dehydration must subsequently be separated, and the production cost of the process is also high

Inactive Publication Date: 2006-07-27
GRUNENTHAL GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This process has the disadvantage that the acid used for the dehydration must subsequently be separated from the reaction mixture by neutralisation and, optionally, repeated extraction.
The resulting salt can lead to equipment corrosion, and side products such as the waste water has a negative effect on the environment, and the production costs of the process is also high.
This process has the disadvantage that the preparation of the chloride compound is carried out with the use of comparatively aggressive chlorinating agents such as thionyl chloride.
Furthermore, the process does not give a satisfactory yield in all cases.

Method used

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  • Process for the dehydration of substituted 4-dimethylamino-2-aryl-butan-2-ol compounds and process for the preparation of substituted dimethyl-(3-aryl-butyl)- amine compounds by heterogeneous catalysis
  • Process for the dehydration of substituted 4-dimethylamino-2-aryl-butan-2-ol compounds and process for the preparation of substituted dimethyl-(3-aryl-butyl)- amine compounds by heterogeneous catalysis
  • Process for the dehydration of substituted 4-dimethylamino-2-aryl-butan-2-ol compounds and process for the preparation of substituted dimethyl-(3-aryl-butyl)- amine compounds by heterogeneous catalysis

Examples

Experimental program
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Effect test

example 1

Preparation of the Bifunctional Catalyst

1a)

[0076] In a round-bottomed flask, 2 g of a sulfonic-acid-group-carrying ion-exchange resin based on a styrene / divinylbenzene copolymer having a divinylbenzene content of 20 wt. %, based on the total weight of the resin, a mean pore diameter of 25 nm and a minimum concentration of active groups of 4.70 equivalents per kg of resin (Amberlyst® 15, Fluka, Switzerland) were suspended in 20 ml of water. 0.3 ml of a palladium tetramine dinitrate hydrate solution having a palladium content of 69.5 mg / ml was then added, and stirring was carried out for 24 hours at a temperature of 80° C. To prepare the palladium(II) tetramine nitrate hydrate complex solution, 10 g of palladium(II) nitrate dihydrate (Fluka) were added to 400 g of ammonia solution (25 wt. % in water) and the mixture so obtained was stirred for 3 days at 50° C. The undesired solid was then separated off by filtration, and the palladium content was determined by ICP-AES, as described...

example 2

Synthesis of (Z;E)-(S)-[3-(3-methoxy-phenyl)-2-methyl-pent-3-enyl]-dimethyl-amine; hydrochloride (2) from (−)-(2S,3S)-1-dimethylamino-3-(3-methoxy-phenyl)-2-methyl-pentan-3-ol; hydrochloride (1)

[0078]

1.0 g (3.4 mmol.) of (−)-(2S,3S)-1-dimethylamino-3-(3-methoxy-phenyl)-2-methyl-pentan-3-ol; hydrochloride (1) and 0.5 g of a sulfonic-acid-group-carrying ion-exchange resin based on a styrene / divinylbenzene copolymer having a divinylbenzene content of 20 wt. %, based on the total weight of the resin, a mean pore diameter of 25 nm and a minimum concentration of active groups of 4.70 equivalents per kg of resin (Amberlyst® 15, Fluka, Switzerland) were placed in a 75 ml stainless steel autoclave. After addition of 15 ml of freshly distilled ethanol, the reaction mixture was stirred for 4 hours at 150° C. in the closed system (at an overall pressure of up to 8 bar). After cooling to room temperature (about 20-25° C.), the catalyst was filtered off. A sample of the filtrate so obtained was...

example 3

Synthesis of (−)-(2R,3R)-[3-(3-methoxy-phenyl)-2-methyl-pentyl]-dimethyl-amine; hydrochloride (3a) and (−)-(2R,3S)-[3-(3-methoxy-phenyl)-2-methyl-pentyl]-dimethyl-amine; hydrochloride (3b) from (Z)-(S)-[3-(3-methoxy-phenyl)-2-methyl-pent-3-enyl]-dimethyl-amine; hydrochloride (2)

[0080]

1.0 g (3.7 mmol.) of (Z)-(S)-[3-(3-methoxy-phenyl)-2-methyl-pent-3-enyl]-dimethyl-amine; hydrochloride (2) and 0.5 g of the catalyst obtained according to Example 1a were placed in a 75 ml stainless steel autoclave. The autoclave was evacuated under a medium-high vacuum and then gassed with argon. Under an argon atmosphere, 15 ml of freshly distilled ethanol were added. A hydrogen pressure of 4 bar was then applied at room temperature, and the reaction mixture was stirred for 4 hours at 150° C. (overall pressure at 150° C. up to 12 bar). After cooling to room temperature, the excess hydrogen was let off and the catalyst was filtered off. A sample of the filtrate was taken and analyzed by gas chromatog...

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Abstract

Process for the preparation of substituted dimethyl-(3-aryl-butyl)-amine compounds. The process comprises dehydration by heterogeneous catalysis of substituted 4-dimethylamino-2-aryl-butan-2-ol compounds, to form substituted dimethyl-(3-aryl-but-3-enyl)-amine intermediates, which are then converted by hydrogenation with hydrogen to substituted dimethyl-(3-aryl-butyl)-amine compounds.

Description

CROSS REFERENCE TO RELATED APPLICATIONS [0001] This application is a continuation of international patent application no. PCT / EP2004 / 006666, filed Jun. 21, 2004, designating the United States of America, and published in Germany as WO 2005 / 000788 on Jan. 6, 2005, the entire disclosure of which is incorporated herein by reference. Priority is claimed based on Federal Republic of Germany patent application no. DE 103 28 316.1, filed Jun. 23, 2003.BACKGROUND OF THE INVENTION [0002] The present invention relates to a process for the dehydration of substituted 4-dimethylamino-2-aryl-butan-2-ol compounds and to processes for the preparation of substituted dimethyl-(3-aryl-butyl)-amine compounds by heterogeneous catalysis. [0003] Opioids, for example morphine, have been used in the therapy of pain for many years, although they cause a number of side-effects, for example addiction, dependency, respiratory depression, impaired gastro-intestinal motility and constipation. They can therefore b...

Claims

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Application Information

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IPC IPC(8): C07C209/68C07C213/08C07C217/62
CPCC07B2200/07C07C213/08C07C217/62
Inventor JAGUSCH, UTZ-PETERHOELDERICH, WOLFGANGWISSLER, MONIKA
Owner GRUNENTHAL GMBH
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