So I'm trying to develop a synthesis going from a primary amide (RNH-COCH3) --> a tertiary amine (RNMe2) (Where R=R) Ideally, I would be able to do this relatively green-ly and/or without specific catalysts.
I'm thinking of something like this:
R-NH-COCH3 + 2 MeI ------> R-N(Me2)-COCH3 ----NaOH----> RNMe2 (+ H3CCO2-)
I'm just not sure whether methyl iodide is a strong enough methylating agent to methylate a weak neucleophile like an amide (let alone dimethylate it!!). But if I hydrolyze the amide --> amine first, then it'll be too reactive, and it'll methylate 3 times! (and/or mix of pdts).
Anyway, I would love to know a) whether this plan would work at all, and b) if not, does anyone have a good idea for either increasing the neucleophilicty of the amide and/or a better methylating agent? (Preferably a way that doesn't break the bank / require rly specific equipment etc)