[xlion_tattoo]

Hi folks!!
I'm trying some aminomercuration on aromatic alquenes (terminal oleofines) to get aromatic amfetamine like. The purpose of my study is to find the mechanistically right role of the aminomercurial and the dependence of its ratio alquene/amine/alquene.
The thing is that if you use Hg(OAc) (the most used acetate salt), it can't be dissolved in THF until MeNH2 or EtNH2 is added. In fact, there is formed a complex qhich remains soluble. Two phases are formed and if you separate them and wieght them, you'll find that all the amine and the Hg(OAc)2 remain in the bottom phase, the water phase.

You run the reaction, and after addition of oleofin, you make the reduction with Mr. NaBH4 (the most widely reduction agent ever known..) getting Hg (0), so the reaction is OK.
The problem is (and let me tell you I feel a bit idiot, 'cause of this): how do you separate it???
---> I have two phases. Once of them is THF + soemthing, and the other water + something. MeNH2 is added in excès and in the reduction you add enough NaBH4 to destroy any aminomercuial formed, so MeNH2 is eliminated by simple evapoartion (just exposing it to air, you smell it).

Books says that best way to separaet aromatic amines like this ones are acidify them. Why? 'cause you attach a H to the nitrogen of the amine (pH 1), making it water soluble. As it remains water soluble, you make siolvent extraction to remove traces of non reacted reagents, plus any other thing. Later, you basify until you reach pH 11, so you take the H from the amine, making it solvent soluble now. You make solvent extraction, distill, and that's all folks (last sentence adapted from Bugs Bunny...I remember it was what it said at the end of cartoons).

the thing is that I think it doesn't work, 'cause two phases (THF and water) are highly coloured, which means that changing pH doesn't help you to change the molecule of phase.

I think I could do more washings with different pHs, or distill both phases by separate, but I don't know if I'm on the good way.
So, what technique, non chromatographic would you use, with this kind of things? How do you separate amine where you have two phases, solvent and water, and appearingly you have the amine like in both (if you take the pH@THF phase, you'll find it's about 11 or more...sorry, my pH paper only arrived until pH 11).

I'd be gratedul if any of you can help me. Playing with pH, I've f***** up a batch.

Ok folks... thank you in advance