taffy - 23-11-2017 at 14:02
Unlike many aldehydes, most imines of ketones form under much harsher conditions such as utilizing (sometimes difficult to handle) dehydrating agents,
prolonged heating or reaction times, and dean-stark traps. However, when it comes to volatile amine gases such as dimethylamine, methylamine, and
ammonia most patent and literature references use either the compressed gases from tanks or in situ generation of the gas and then condensed with dry
ice.
I'm currently attempting to condense arylalkyl ketones with these amines however utilizing the salts is appealing to me since I don't plan on using a
bubbler setup for the gases unless I have to. I've seen one ref. that utilized TiCl4 (which I'll attach) for condensation of ketones with amine
hydrochlorides in good yields but as TiCl4 is a bit difficult to source, and not exactly fun to work with, I'd prefer to opt for a modified procedure
of some sort that uses less toxic reagents for amine salts in regards to ketimine formation.
[Edited on 23-11-2017 by taffy]
Attachment: Ketimine1.pdf (368kB)
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[Edited on 23-11-2017 by taffy]