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Botched Foxy

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JedZed:
Hey, gang-
     I was talking on a cordless phone recently and happened to pick up snippets of the conversation of SWIM.  He said that he deacetylated some melatonin by refluxing in ethylene glycol with NaOH for an hour, cooled, & tried to extract with DCM.  On addition of salty water to break the accursed emulsion he got, he ended up with a pile of beige crystals, which he dried.
     These he then stirred with K2CO3 in acetonitrile (practically identical polarity with DMF) but accidentally added about a tenfold excess of iPrBr.  He let the pot stir for an hour and then attempted to crash out some product by adding water.  Nothing happened- no crystals, no oil, nothing.  Not even a little bit of the bromide in an organic layer.
      Knowing a little bit (a very little bit) about chemistry myself, I'm wondering if this poor guy got a quaternized salt, or could he have broken the methoxy ether in the amide hydrolysis?  Neither of these seems likely, as the first case would have to overcome a good bit of steric hindrance, and in the second case, he would've had a phenolic sodium salt at the end of the hydrolysis, which I think would've remained in solution.
       Any input for this guy, in case I ever pick up one of his conversations again & maybe can try to help him out?

CHEM_GUY:
Okay, it doesn't look like you added after the attempted alkylation.  My thought is that Foxy is dissolved in the MeCN and untill you add an acid it is going to stay there.  Try add HCl, the foxy will go to the water and then evaporate to leave the crystals. 

This post is for informational purposes only an is not intended to facilate illegal activity.

CHEM_GUY:
FIRST LINE SHOULD READ:
 "It doesn't look like you added an acid after..."

This post is for informational purposes only an is not intended to facilate illegal activity.

JedZed:
No, this wasn't an attempt at a phase separation ('sthat what it's called?).  MeCN seems miscible with, or at least very soluble in water.
   It would seem that a free base 3* amine would not be soluble in

JedZed:
Thanks for the advice, Teo; I'd been wondering about the equation for that rxn.  You've posted it before, I think in the Breath of Hoax? thread.
     Anyhow, I saw that guy buying melatonin tabs and ethyl rubbing alcohol at the corner pharmacist's the other night.  He did a DCM extraction & the organic layer yellowed- signifying extraction, he was telling the clerk, but, he went on, then he went and spilled the MeCl2 and his product.  He felt very silly.
      I think it's very interesting that foxy freebase is so soluble in

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