Process for the preparation of secondary and tertiary amines

Details Process for the preparation of secondary and tertiary amines Process for the preparation of secondary and tertiary amines

C - Chemistry, Metallurgy

07

C

C07C 209/00 (2006.01)

Patent

CA 2394519

N,N-disubstituted amines in which the amino nitrogen atom is bound to the carbon of an aromatic ring disubstituted in the positions ortho to the carbon atom, are prepared by allowing a primary amine and a compound in which an ortho, ortho-disubstituted aromatic compound carrying a nucleofuge substituent, to react in a basic environment in the presence of a catalytic palladium(0) complex and a ligand, the ratio of palladium complex to ligand being greater than at least 1:1. A typical embodiment involves the reaction of 2-methyl-6-ethylphenyl-trifluoromethylsulfonate and (S)-1-methoxy-2- aminopropane in the presence of bis(dibenzylideneacetone)palladium, tri-tert.- butylphosphine, and sodium tert.-butoxide to yield (S)-N-(1-methoxyprop-2-yl)- 2-methyl-6-ethylphenylamine.

Selon l'invention, on prépare des amines N,N-disubstituées dans lesquelles l'atome amino-azote est lié à l'atome de carbone d'un noyau aromatique disubstitué en positions ortho par rapport à l'atome de carbone, en faisant réagir une amine primaire et un composé renfermant un composé aromatique ortho ou ortho-disusbtitué comportant un susbtituant nucléofuge dans un environnement basique et en présence d'un complexe du palladium(0) catalytique et d'un ligand, le rapport complexe du palladium/ligand étant supérieur à 1:1 au moins. Selon un mode de réalisation typique, on fait réagir un 2-méthyl-6-éthylphényl-trifluorométhylsulfonate et un (S)-1-méthoxy-2-aminopropane en présence de bis(dibenzylidèneacétone)palladium, tri-tert.-butylphosphine et de tert.-butoxyde de sodium, de manière à obtenir une (S)-N-(1-méthoxyprop-2-yl)-2-méthyl-6-éthylphénylamine.

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