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Abstract
The monomethylation of anilines was achieved in high yield from the reaction of 1,3,5-triphenylhexahydro-1,3,5-triazines with BH3·S(CH3)2 followed by hydrolysis.
Notes
Reductive monomethylation of 1,3,5-trialkylhexahydro-1,3,5-triazine was not successful due to its harsh condition to hydrolyze N-methylaminoborane and relatively lower reaction yield.
Though less than 3 mol equivalents of BH3·S(CH3)2 gave similar result in a few cases the procedure with 4 mol equivalents was generally applicable and quite effective in most cases.
The large scale reaction with 50 mmol of 1,3,5-triphenylhexahydro-1,3,5-triazine was also quite successful in 91% yield.