N-dealkylation of tertiary amines

Details N-dealkylation of tertiary amines N-dealkylation of tertiary amines

C - Chemistry, Metallurgy

07

D

260/269, 260/595

C07D 489/02 (2006.01) C07C 37/055 (2006.01) C07D 211/78 (2006.01) C07D 221/18 (2006.01) C07D 295/023 (2006.01) C07D 451/06 (2006.01) C07D 489/08 (2006.01) C07J 9/00 (2006.01)

Patent

CA 1037062

ABSTRACT OF THE DISCLOSURE A method for the N-dealkylayion of tertiary amines which involves replacing an N-alkyl group of the tertiary amine with a vinyloxycarbonyl group by reaction with, for example, vinyl chloroformate to form a vinyloxycarbonyl amide, followed by cleavage with, for example, a mild acid to split off the vinyloxycarbonyl group and obtain the secondary amine. Such tertiary amines also containing alcoholic or phenolic hydroxyl groups can simuitaneously be provided with hydroxyl group protection by formation of vinyloxycarbonyl ester groups which are stable under the mild acid cleavage conditions and which are removable with base or strong acid. The method has particular use in the syntheses of various tertiary amine compounds involving replacement of an alkyl group in a starting tertiary amine with another N-sub

209765

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