Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Patent
2000-02-22
2000-10-24
Stockton, Laura L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
544173, 544106, 544170, 560 42, 564390, C07D26530, C07C22900, C07C21500
Patent
active
061369721
ABSTRACT:
A Mannich base intermediate for 2-[(4-heterocyclic-phenoxymethyl)-phenoxyl]-alkanoates and methods for its preparation are provided. A method for preparation of an alkyl 2-[2-(secondary amino methyl)-5-alkylphenoxy]-alkanoate comprises the steps of: reacting a mixture of m-alkyl phenol, a secondary amine, and an aldehyde, with or without a catalyst, in a first solvent at reflux temperatures to form a 2-[(secondary amino)methyl]-5-alkylphenol. That product is then reacted with an alkyl 2-haloalkanoate, and an alkali metal carbonate, with or without a second catalyst in a second solvent at reflux temperatures to form the 2-[2-(secondary amino methyl)-5-alkylphenoxy]-alkanoate. The aldehyde may be paraformaldehyde, aqueous formaldehyde, formaldehyde, or polymerized acetal derivatives thereof. The first solvent may be acetonitrile or toluene. The catalyst may be an acid catalyst or a base catalyst. In the preferred embodiment the Mannich base is a 2-[(secondary amino)-methyl]-5-alkylphenol, or a 2-[2-(secondary amino methyl)-5-alkylphenoxy]-alkanoate.
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"Synthesis of 2-Aminomethyl-5-Butylphenols", Faculty of Engineering, Toa University, Ichinomiya Gakuen-cho, Shimonoseki-shi, Yamaguchi, 750, Japan, Kyushu Daigaku Kino Busshitzu Kagaku Kenkyusho Hokoko (1997), 11(2), 125-129 (CA 130:168047, 1999).
Crispino Gerard A.
Diener Mark R.
FMC Corporation
Stockton Laura L.
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