[OrganicDan96]

DMAP is actually a terrific base for aminations, but probably not necessary here.

its not just abase but an activator as it's nucleophillic

[wildfyr]

DMAP is actually a terrific base for aminations***, but probably not necessary here.

its not just abase but an activator as it's nucleophillic

Completely true, it creates a transient activated ester, as in DCC/DMAP amidation.


**this should say amidation, not amination.

[rolnor]

You get a acylpyridinium ion, pyridine is similar as DMAP.

[wildfyr]

DMAP is a better nucleophile than plain pyridine. Also it doesn't stink as bad and is often used in subequimolar amounts. .

Quick tip for anyone trying to remove pyridine or other pyridine like molecules from a reaction that is acid sensitive: copper sulfate extraction.

[hypervalent_iodine]

DMAP is a better nucleophile than plain pyridine. Also it doesn't stink as bad and is often used in subequimolar amounts. .

Quick tip for anyone trying to remove pyridine or other pyridine like molecules from a reaction that is acid sensitive: copper sulfate extraction.

Could not recommend this enough. Some of my more difficult amidations using pyridine went from ~40% to ~85% yield just by changing the work up to 1M CuSO₄.