Processes for the preparation of aminoethoxybenzyl alcohols

a technology of aminoethoxybenzyl alcohol and process, which is applied in the preparation of amino-hyroxy compounds, chemistry apparatus and processes, and organic chemistry, etc., can solve the problems of expensive and difficult solvent handling

Inactive Publication Date: 2008-08-28
WYETH LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This method provides a more efficient and cost-effective synthesis of aminoethoxybenzyl alcohols, suitable for producing pharmaceutical intermediates like matrix metalloproteinase and TACE inhibitors, by eliminating the need for unstable reagents and using more affordable solvents, enabling larger-scale production.

Problems solved by technology

The multi-step procedures also reportedly employ dimethylformamide (DMF) as solvent, an expensive and difficult solvent to handle, especially in large scale preparations.

Method used

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  • Processes for the preparation of aminoethoxybenzyl alcohols
  • Processes for the preparation of aminoethoxybenzyl alcohols
  • Processes for the preparation of aminoethoxybenzyl alcohols

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PREPARATION OF [4-(2-HEXAMETHYLENEIMINO-1-YL-ETHOXY)-PHENYL]-METHANOL

[0091]

Preparation of 1-Hexamethyleneimin-1-Yl-2-Chloro-Ethanone

[0092]Hexamethyleneimine (76.4 kg) was added to a solution of 2-chloro-acetyl chloride (43.5 kg) and toluene (200 kg) maintaining the temperature between 0° C. and −3° C. At the end of the reaction, water (57.8 kg) was slowly added and the resultant mixture was heated to 20-25° C. The aqueous layer was discharged and the organic layer containing 1-chloroacetyl-hexamethyleneimine was used in the subsequent step without any further purification.

Preparation of 4-(2-Oxo-2-Hexamethyleneimino-Ethoxy)-Benzaldehyde

[0093]The phase transfer catalyst tricaprylmethylammonium chloride, K2CO3 (58.5 Kg), 4-hydroxybenzaldehyde (50 kg) and toluene (8.5 kg to rinse the lines) were added to the solution of 1-chloroacetyl-hexamethyleneimine obtained from the previous step. The resulting mixture was heated to reflux temperature and water was removed by azeotropic distillati...

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Abstract

The present invention provides processes and intermediates for the preparation of aminoethoxybenzyl alcohols of Formula I useful in the production of pharmaceutically useful compounds.

Description

CROSS REFERENCE TO RELATED APPLICATIONS[0001]This application is a division of U.S. patent application Ser. No. 11 / 329,503 filed Jan. 11, 2006, which claims the benefit of priority from provisional U.S. Patent Application Ser. No. 60 / 643,505 filed Jan. 13, 2005, each of the aforementioned applications is incorporated herein in its entirety.FIELD OF THE INVENTION[0002]This present invention relates to processes and intermediates for the preparation of aminoethoxybenzyl alcohols that can be used in the preparation of pharmaceuticals.BACKGROUND OF THE INVENTION[0003]Aminoethoxybenzyl alcohols are widely useful as intermediates for the preparation of various pharmaceuticals. For example, conversion of the benzylic alcohol to a halogen results in the appropriate intermediate for the preparation of indole based estrogen receptor modulators as described in, for example, U.S. Pat. No. 5,998,402. Additionally, similar benzylic halides that can be derived from their corresponding benzylic alc...

Claims

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Application Information

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Patent Type & AuthorityApplications(United States)
IPC IPC(8): C07D223/04C07C215/28
CPCC07D295/088C07C213/02C07C217/20C07C213/08C07C217/14
InventorALLEGRINI, PIETROBARRECA, GIUSEPPESORIATO, GIORGIO
OwnerWYETH LLC