My compound has a secondary amine in aromatic system. I dissolved it in Acetone/DCM (2:1) and added dropwise 2M solution of HCl in Ether, then slowly precipitate appeared and on TLC the starting material completely consumed (all material at the bottom of TLC). Then I just evaporated solvent and added Chloroform/Acetone to dissolve it again but when I checked TLC the salt formed is again back to the starting material and nothing at bottom of TLC.
Can HCl salt form of compound can go back to original easily? How to overcome this problem?
When I treated same compound with CH3I, it is going good and stable enough. Only the problem is with making HCl salt.
Thank You.
Some of the salt form compounds can be eluted in the free form if you pass through silica, also sometimes salt form and free form can have safe Rf value so I recommend NMR analysis before coming to conclusion.
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