[baum0372]

I have a compound with a highly basic amine (monosubstituted ethylenediamine).  When I isolate the compound, I am able to recrystallize from ether, however, upon a second recrystallization, I have a lot of new insoluble material.  It's pretty humid out and I am thinking that its the hydroxide salt of the amine, which is likely insoluble in ether.

My question is how does one work with compounds such as these?  Is there a volatile organic base I can add to deprotonate?  Or must I use a glovebox?  Thanks.

[discodermolide]

It may be the amine carbonate salt, from CO₂ in the humid air.
Ether picks up a lot of moisture so it's not ideal for re-crystallisations, di-isoproplyether may be better.
Why not make the HCl salt of your amine and crystallise that?

[baum0372]

My next step involves making the TMS protected primary amine, and from what I have heard, the salt form is not as amenable to protection as the free amine.  And actually I didn't specify, but I had been using diisopropyl ether.  Is there any way to free the carbonate salt to the free amine?

[discodermolide]

Obviously is you are going to make the TMS amine you will need to convert the salt, HCl or carbonate to the free base.  Treatment with NaOH should sort that out.  Or use triethylamine if that is not an option.
Your amine may be more stable as the HCl salt anyway.