here is my problem..
i'm trying to synthetise this quaternary ammonium salt.
I have some troubles for the first step... I can't isolate this amine, because it's really volatil. I have tried to add picric acid, or oxalic acid, but nothing precipitate. Then I added a solution of HCl in diethylether, and I don't have any precipitate of chlorhydrate, just some fumes over the ether, which seems to be my amine chlorhydrate!
I have tried to do the same reaction but like this : dimethylamine.HCl + Bromobutene (Dichloromethane/Et3N). And then, I can precipitate Et3N.HCl + N,N-dimethylhomoallylamine.HCl (it seems that the presence of the Et3N.HCl precipitate facilite the correct precipitation of my amine).
Then I have put my mixture of these two amines in the following step... Unfortuatly, I have almost 100 Et3N+CH2COOK for one of my desirated product...
Of course, I could try to separate these two compounds by preparative HPLC... But do you think there is a trick to isolate my amine from the first step (reaction between allylMgCl and Eschenmoser's salt?)