[ResearchGrad]

I'm working with a tetraammonium salt. I need to convert it to free amines at all 4 positions.  Compound is only soluble in methanol. I do not want to use aqueous NaOH and extract with organic solvent as amines tend to be in the aqueous phase.  I read from a previous thread regarding use of NaOCH3. It sounds reasonable to filter off NaCl, but what happens to excess NaOCH3?  NaOCH3 is a solid and is soluble in methanol or ethanol, how to isolate that from the free amine? Should I run this through a column?

Your help is appreciated.

[ResearchGrad]

I'm working with a tetraammonium salt. I need to convert it to free amines at all 4 positions.  Compound is only soluble in methanol. I do not want to use aqueous NaOH and extract with organic solvent as amines tend to be in the aqueous phase.  I read from a previous thread regarding use of NaOCH3. It sounds reasonable to filter off NaCl, but what happens to excess NaOCH3?  NaOCH3 is a solid and is soluble in methanol or ethanol, how to isolate that from the free amine? Should I run this through a column?

Your help is appreciated.

[g-bones]

It doesn't seem unreasonable to me to simply use the ammonium salt in the formation of the amide as long as you have a whole slew of alternative base.  for instance, if you run your condensation in something like 1:1 pyridine:solvent or even with pyridine as the solvent alone, you will get an equilibrium from the ammonium salt to the pyridinium and the free amine which can then go on to do further chemistry.  this would be especially useful if the amide formation is acid catalyzed because you would be using the proton you already have.  even if your salt isn't all that soluble in a particular solvent, any amount that does enter the solution will quickly form the free amine (again, a function of an equilibrium between the large amounts of pyridine and small amounts of amine) thus pulling more ammonium into solution since it is consistently being pulled from equilibrium by deprotonation.  hope this helps