Alright so the old man down the road finally decided to give this a go, heres what I witnessed:
-1.1g MDA.HCl basified, extracted twice with DCM
-DCM stripped off, the remaining base then taken up in MeOH
-To this was added 0.38ml formalin (though I screwed up the pipetting of such a small amount, inevitably this caused an excess)
-The solution of MDA formaldehyde imine was then left in a dropping funnel for ~1hr.
-in an RB, 120mg of HgCl2 (originally started with 20mg, then kept adding more to get a decent reaction rate) and ~0.2g aluminium were amalgamated in a solution of MeOH.
-The amalgam mixture was brought to ~50°c and the MDA formaldehyde imine solution then dripped in.
-Reaction ran for ~2hrs, when most of the aluminium was used up, keeping in mind I used a decent excess of aluminium.
-Reaction volume was doubled using a solution of NaOH, then filtered to remove solids.
-The remaining liquid was extracted twice with xylene.
Yet to do the final work up to get the final result and yield (if any), will post when this is done. This is my first time witih Al/Hg and I must say I already dislike working with HgCl2, its a pain in the ass because of the precautions needed with cleaning etc. Seems like Al/Ga could be used, though im yet to find any good posts regarding its use (if anyone has any, please share).
Reference: http://www.erowid.org/archive/rhodium/chemistry/amphetamine.methylation.html
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Final workup has just been completed and yielded absolutely nothing. Pretty disappointing.
Guess I might try again when I have more starting reagents to play with and up the scale a bit.
Not really sure what went wrong either, I was expecting something, even if it was a poor yield.
The problem obviously isn't in the reaction procedure. Even if we assume no reaction happened at all, the fact that your xylene xtrxn didn't give you back anything should make it clear to you that there wasn't anything in the xylene to extract: even in the total failure case, a correct work-up will give you back a decent proportion of the starting material. If I had to guess, the MDXA crashed out when you added NaOH and water to the rxn mixture, which is why none of it made it into the xylene.
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Klute from memory says purification of amine can be done via distillation.
-I find this unsuitable due to working at 10 mmole scale, so instead I tried doing a mild A/B hoping it would leave behind the aldehyde and bring over the secondary amine. The indications looked good, upon basifying the acidic aqueous layer, much table salt (presumably) was visually seen and again the smell of an amine was present. A non polar extract yielded a slightly yellow solution.
"I didn't listen."
A handy tip: basify after you add the first portion of NP solvent. That way your amine doesn't end up stuck to the bottom of the glass.
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Methyl bromide generated on demand for methylation. Does anything think this would not work in replacing methyl tosylate?
KI is an effective catalyst for any alkyl halide mediated methylation:
R-X + I- --> R-I + X-
R-I + R'- --> R-R' + I-