Lets say someone wanted a non-polar solution of methylamine and a methylenedioxyphenylacetone to reductively alkylate with borohydride or triacetoxyborohydride.. If xylene is added to an aqueous solution of methylamine-HCl/NaOH, would the free methylamine be much more soluble in the xylene?

I doubt it.  I would think methylamine is not very soluble in Xylene and would mostly stay in the aqueous layer.

True, it's not greatly soluble in aromatics (much better in ether, methanol, water, etc), but you could really push it out of the aqueous with conc NaOH... you should be able to put 5-10g MeAm per 100g aromatic... HOWEVER... I would highly recommend you gas it cold so you can see how much it really is picking up.

Thanks.. So, I guess I'd be better off with diethyl ether.