[Gpour]

So I'm making a series of anilines in my lab. Most of them turn out ok, but one of them is giving me confusing results. I'm trying to form the mono substitution product of morpholine with 1,3,5 trihydroxy benzene dihydrate (phloroglucinol) in a 1:2 Toluene/BuOH solvent system. The TLC doesn't seem to be showing any product forming after a long reaction time and the reaction color goes from colorless to orange. I've done the same reaction with piperidine before, and while I knew that morpholine was less nucleophilic than piperidine I didn't think that the difference would be so drastic as to prevent it from going forward. Any suggestions, tips, insights would be greatly appreciated.

[Archer]

I suggest to use anhydrous phloroglucinol, if you can't get it then dry what you need under vacuum over P₂O₅ in a drying pistol or similar equipment.

I have had plenty of reactions working once I discovered this water of crystallisation in phloroglucinol was interfering with it.