Has anyone successfully attempted this?

I've tried it a few times with zero results.

It is theoretically possible.

I've tried both concentrated and dilute solution of KOH and NaOH under reflux(max. 30 min). The only change was the color.

I think the trick may be to reflux for a LONG time. I'd be interested in hearing from someone who has actually successfully pulled this off.

I can't remember exactly. It's all clearly outlined in my organics book.

If memory serves me right it's not nearly as effective as alkaline hydrolysis.

Something to do with equalibrium I think. I could be entirely wrong about that.

I just looked it up.

"typical [amide] hydrolysis conditions involve prolonged heating in 6M HCl or 40% aqueous NaOH"


I'm almost 100% sure now that it's an issue with heating. Under reflux for ~24hrs. just to be safe, DE should form.

That's the only variable I left out during my runs, the time factor. 

Also another thing is that DEA is immiscible in water which is why a co-solvent may speed up the process significantly causing DEA and EG to mix in all parts with the water instead of across the surface of the phases where the DE and water meet. One such example is ethylene glycol. I'd experiment with it myself but I'm strapped for cash at the moment for my other runs I'm working on.

I'd really like to see someone pull this off successfully though. DEA is one of the hardest precursors to aquire for LSD synthesis. Buying DEA is out of the question. Too risky for a swimmer like myself.

However, if one could simply just buy some DEET bug spray(100% concentrations are out there), ethylene glycol(antifreeze...you'd probably have to distil it), the rest is easy.

A pedantic note:

The hydrolysis mechanism uses either the hydroxide ion (in basic hydrolysis schemes) or the proton (in acidic hydrolysis schemes), not the 'alkali metal.' The metal ion is a spectator ion.

Hydrolysis of Amides
Hydrolysis of Esters

Uhm, so, if I mix table salt (NaCl, which contains an alkali metal ion as does NaOH) with your amide, will that work to HYDROlyze it? No. To get hydrolysis, you need water, which exists in the equilibrium


I would be interested to see the textbook that uses the phrase, 'alkali metal catalyzed hydrolysis of an amide.'

Yes, the reaction is reversible. It's called esterfication, which uses only a strong acid. That won't happen in your situation, because there is too much water in the system.


The extra water will drive the equilibrium to the left.

Topic spit, I left the posts that contain information, discussion, or debate while I have put posts that begin the flaming into the Vacuous Posts section.

I don't think he ever said, or implied to use an alkali metal in  elemental form for this reaction. Obviously he meant their hydroxide as he had stated in the first he had attempted to use KOH and NaOH.

I think it is ok to say that amide hydrolysis is encouraged by either acidic, or basic solutions.

Check this thread. Mild success is reported, though through an unoptimized procedure. I really should pull out my glassware and try it.

Poison, if you are still experimenting with this, try 30% HCl + 98% DEET with microwave irradiation. You could have a nice yield of diethylamine in the time it takes to reheat last night's left overs. 

I've never seen it mentioned anywhere... so it may not work. If I was to work on this, I'd give it a shot though.

Edit: It'd prolly go something like this:

http://www.4shared.com/file/96253082/9c2fc6d5/microwave_peptide_hydrolysis.html

That ref. is beautiful. I was going to respond last night but I felt extremely ill.

I'll definitely take a swing at it once I get my financial problems sorted out.

I'm not sure of the output of my microwave but at the highest setting with DEET with an excess con. HCl so as to keep the equalibrium balanced, in a closed ureactive vessle checked periodically every 30 seconds for 10 minutes *should* work based off the ref.

A co-solvent wouldn't be necessary either since the irradiation will take care of that by cleaving the DEET. The only thing is you'd almost definitely have to do this outside or under a hood. Diethylamine has a BP at ~56C and DEET has one way into the ~200-300C range...I haven't checked this so you might want to error correct them since I'm just going off my memory the last time I tried this. The HCl is the biggest problem. The hydrogen Chloride fumes will be extremely nasty so proper lab safety is important. It should probably be done outside, or under a hood.

Also, the vessel could cause some issues. You could throw the whole mess into a bomb or another unreactive, threaded vessel that can withstand the pressure. The hard part is it'd have to be made out of something non metal since it'll be in the microwave(bad combo). An alternative would be to just scale it down REALLY SMALL. Try maybe 5ml DEET + 10ml muriatic in a big glass(HDPE maybe?...it might melt.) jar. This way the pressure inside the vessel will be insignificant with the amounts being worked with.

I think 10 minutes on max heat should be perfect. Then one could distil the diethylamine off by short path distillation with a 3-way. I wonder how the yields would be.