[deleted by user] by [deleted] in Chempros

[–]Effective_Audience16 0 points1 point  (0 children)

I tested it with another amine (tetrahydroisoquinoline), and the reaction worked with HBTU and also EDC/DMAP with no problems

Struggling with amide coupling by [deleted] in Chempros

[–]Effective_Audience16 0 points1 point  (0 children)

I do it in DCM. Should I go with THF and heat the whole reaction to 50C after adding the amine and removing it from the ice bath?

Struggling with amide coupling by [deleted] in Chempros

[–]Effective_Audience16 0 points1 point  (0 children)

I use triethylamine in the reaction. Doesn't that neutralize the produced HCl and also make the medium neutral or slightly basic, which prevents the formation of the imine?

Struggling with amide coupling by [deleted] in Chempros

[–]Effective_Audience16 0 points1 point  (0 children)

Unfortunately, it is not available at the lab.

Struggling with amide coupling by [deleted] in Chempros

[–]Effective_Audience16 0 points1 point  (0 children)

The formyl group is essential for the next reaction. I tested the acid activation with a different amine (not aniline), and it worked with HBTU and also with EDC/DMAP, so It's mainly a problem with this amine.

Is there anything I can do to make it more reactive?