[rolnor]

I can not find any examples on scifinder where peracetic acid is used to oxidize tertiary amine to N-oxide. I see many examples with H2O2 or m-CPBA. One example in Fieser and Fieser where they make pyridine-N-oxide and in this case the acetic acid is easily removed by distilation because the pyridine-N-oxide is weaker base then trialkylamineoxides I am interested in. I have oxidized trialkylamines with peracetic acid and washed the acetic acid away with carbonate solution so I know it works, its possible to get the N-oxide pure in this way but I would like to see if it has been done in the literature before.

[chenbeier]

Maybe this helps.
It is a old german paper.

At chapter 1.4.1 Peressigsäure peracetic acid is decribed for the oxidation of amins:

https://books.google.de/books?id=1TOGAwAAQBAJ&pg=PA416&lpg=PA416&dq=aminoxide+peressigs%C3%A4ure&source=bl&ots=xPV2HkfSk3&sig=ACfU3U2KxxXP129tZ2zHQ4hxUVqpgQDgAw&hl=de&sa=X&ved=2ahUKEwjehIm13vXhAhUSqaQKHZtND2YQ6AEwCXoECAkQAQ#v=onepage&q=aminoxide%20peressigs%C3%A4ure&f=false

[rolnor]

Great! Thank you. There is one exampel in the reference where they use peracetic acid and isolate the free base, thats all I wanted. I give you a "Mole snack" chenbeier.

[wildfyr]

Just curious, what was wrong with using hydrogen peroxide or mcpba?

[rolnor]

Hydrogen peroxide is so slow, needs heating and long reaction time when you have stericaly hindered amine.
M-CPBA is more difficult to remove, needs chromatography.

[wildfyr]

mcpba can be removed by doing a sodium thiosulfate wash to quench it all to the benzoic acid followed by a bicarb wash.

https://www.odinity.com/epoxidation-of-geraniol/

Peracetic acid, is volatile, somewhat more dangerous, and less reactive than mcpba

[rolnor]

Then its probably no problem with m-CPBA. Peracetic acid is easie to messure with syringe, reaction is done in 2min in my case. Thanks for the reference wildfyr, I give you a mole snack.
In my case I make N-oxide wich is very polar, partially water-soluble så I use DCM, the salt of benzoic acid could be soluble in in DCM, at least partially. In the referance they make epoxide.