Here are the numbers I'm using for the amination.  If someone would kindly check to make sure it all lines up I'd really appreciate it.

#1 - 43.6g Iodosafrole (0.150 mol)
Shooting for a 20x excess of NH3 at 15% concentration in IPA...

161g NH4Cl
181g NaOH in H2O (1.5x excess of NH3)
291g IPA
Gassing should add 51.3g for a total of 342g


#2 - 19.9g Iodosafrole (0.0686 mol)
Shooting for a 10x excess of MeNH3 at 15% concentration in IPA...

46.3g MeNH3.HCl
41.2g NaOH in H2O (1.5x excess of MeNH3)
121g IPA
Gassing should add 21.3g for a total of 142g

Also why would it matter its bp for salting? You salt then filter and repeat until you decide its not worth it to salt anymore. Would it just be for evaporating the solvent quicker?

Exactly!  Also I don't like working with Toluene/Xylene because that shit gets everywhere and the smell lingers for a long time.

edit: Looks like MDMA/MDA.HCl is soluble in DCM.  The gassing can be done in DCM but you won't see any crystals until evaporation.  This would probably result in dirty crystals since there will be other stuff in the DCM (like....safrole).  So I'll go with Toluene.

This is an awesome thread. I can't wait to see the results! I've been up to this point many times and even yielded amine freebase from this route but have yet to yield HCL in attempts to gas. Keep us posted! Good Work! Very thorough...

_Pbint_

/impatiently taps fingers/

Had a sneaking suspicion and decided to take a density of the liquid I was about to gas.  Turns out I accidentally poured some NITROMETHANE in there!  Replaced it with IPA.  Dripped NaOH over MeNH3 for about 5 minutes.  Combined that and the iodosafrole and INSTANT GOLDEN YELLOW!!! 

Going to let it react for a bit, then start the workup.

Any thoughts on how long I should dry the Toluene extraction with Na2SO4 before I salt?

Bad news.  Gassing produced: nothing.

Oil after evaporating IPA


Added water, basified, and extracted with Toluene
Aqueous layer on left, organic on right


Ready to gas
Dried the toluene/oil with Na2SO4 for about 45 minutes before this


Gassing
It turned a red/brown/purple color while gassing


No precipitate.  Ok, maybe a teeny tiny bit at the bottom, but so little that I wouldn't be surprised if it were just Na2SO4 that made it through the filter.  Any chance the precipitate is locked up in the Toluene?  I may evaporate what I have and see if anything shows up.

I'm sorely disappointed.  Advice?

Why did you not do a proper acid base workup on your crude supposed amine? Dissolve it all in dilute HCl and wash away all the shit that is not an amine, with PhMe/MTBE/Et2O (not CH2Cl2 if particular amine.HCl is soluble). Then basify the aqeous and you will also be able to see by the clouding/oil if you even have anything.. Extract your cleaned amine with CH2Cl2, don't even have to wash with brine or anything but I always do with brine... Dry, filter, evaporate. Then if you want to gas, take it up in distilled, dry toluene and proceed as usual.

Alternatively, take it up in iPrOH and neutralize with conc HCl, evaporate the solvent and reevaporate with more iPrOH once or twice to remove water and excess HCl, and recrystallize the material finally. This is my preferred workup of every single amine, no matter what it is.

Agreed, your toluene looks very wet. Probably didn't use enough Na2SO4. Also, be sure to extract from the Na2SO4 three times.

When the toluene is dry, it should be completely clear, not cloudy, and the Na2SO4 should swirl around freely, not clump up.

What pyramid suggested is probably your fastest and easiest way to get everything out at this point, since you've already gassed it wet. Probably best not to try drying it now, as MDMA*HCl would crash out and get filtered out along with the drying agent, Na2SO4 in your case. Do the aqueous extraction with some mild 1M HCl, evaporate it, and follow this recrystallization procedure:

http://127.0.0.1/talk/index.php/topic,3367.msg35553.html#msg35553

Bear in mind that toluene azeotropes with water - 80% toluene, 20% water by weight. That's a lot. Na2SO4 can complex up to 10 moles of water, but in practice it doesn't work out this way, you need a lot more than you'd expect to dry a solvent. Na2SO4 doesn't dry things as fast or as completely as MgSO4, though it's easier to remove as it's not powdery, therefore it's more convenient to work with and generally preferred. It usually takes 5 minutes or so for Na2SO4 to pick up all the water it's capable of stripping out of solution.

The way Assyl would approach preparing to gas would be to do the initial extraction with DCM (it does azeotrope with water, but it only picks up about 1% water by weight), dry it with Na2SO4, pull off the solvent, then dump in the toluene (extracting 3x from the Na2SO4, of course) and proceed as usual.

DCM is fantastic for extractions in general. It speeds up the process, as it's heavier than the aqueous layer (no reloading the sep funnel after each extraction), it's volatile, and it doesn't pick up much water. It's also insoluble in water, unlike ether, which can dissolve into the aqueous layer in amounts up to 8% by weight. It also tends to have more solvating power than other water immiscible solvents, such as toluene, or ether especially.

Not sure where this procedure went wrong.  A couple thoughts..

-There could have been water in the IPA during amination.  In the rush of getting everything going I think I used 99% IPA that hadn't been dried
-The density of my oil after bromination was only 1.11 g/ml, suggesting that I may have had little or no bromosafrole

However, a cold drop of H2SO4 applied to my iodo turns a brownish burgundy, which is in line with what jon has said.

I still have the larger batch if iodo.  I'll be running it through the procedure again, but will make sure I'm using fully dry IPA.

That's too bad, I was really rooting for you bjuice.    Here's hoping you find some success soon!

I just wanted you to know that I found this thread very fascinating and informative, even if it didn't yield your intended results. Please keep posting your findings here!