PROCESS FOR THE PREPARATION OF 2-AMINO-3,5-DIBROMOBENZYL AMINES
1. A process for the preparation of 2-amino-3,5-dibromobenzylamines corresponding to the following general formula see diagramm : EP0130224,P11,F1 in which R represents hydrogen or C1 -C3 alkyl and R' represents an optionally substituted C1 -C5 aliphatic radical, an optionally substituted C5 or...
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Zusammenfassung: | 1. A process for the preparation of 2-amino-3,5-dibromobenzylamines corresponding to the following general formula see diagramm : EP0130224,P11,F1 in which R represents hydrogen or C1 -C3 alkyl and R' represents an optionally substituted C1 -C5 aliphatic radical, an optionally substituted C5 or C6 cycloaliphatic radical or an optionally substituted phenyl group, and physiologically compatible salts thereof with inorganic or organic acids, characterized in that a) an anthranilic acid alkyl ester corresponding to the following general formula see diagramm : EP0130224,P11,F2 in which X is a lower alkyl group, is brominated in the presence of an oxidizing agent to form the 3,5-dibromoanthranilic acid ester III see diagramm : EP0130224,P11,F3 b) the 3,5-dibromoanthranilic acid ester III is reacted with hydrazine to form a hydrazide corresponding to the following general formula see diagramm : EP0130224,P11,F4 c) the hydrazide IV obtained is reacted with a sulfohalide to form N-(2-amino-3,5-dibromobenzyl)-N'-sulfonyl hydrazide corresponding to the following formula see diagramm : EP0130224,P11,F5 in which Y is an aliphatic or aromatic radical, d) the sulfonylhydrazide V obtained is reacted in alkaline medium with a primary amine corresponding to the following general formula H2 N-R' in which R' is a defined above, to form the Schiff's base VII see diagramm : EP0130224,P11,F6 e) the Schiff's base VII obtained is hydrogenated to the compound of general formula I and, optionally, f) to prepare a compound in which R is C1 -C3 alkyl, is alkylated with an alkylating agent and, optionally, g) the compound obtained in step e) or step f) is converted into its salt in known manner. |
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