I am working on pyridylamine compounds as nucleophiles for a reaction. During the work, I encountered an amine which is in the form of a Hydrochloride salt. To perform my reaction, I need to completely remove it from the salt state and use its free amine. I can't extract it with the help of dichloromethane and water because the solubility of the this amine in free form is 20 times its salt state in water.
There are two approaches for such reactions:
1) You can use Na2CO3 or NaHCO3 or any weak base to neutralize the hydrochloride salt while simultaneously monitoring the pH using pH paper.
OR
2) You can use KH2PO4 as a buffer to neutralize the effect of HCl and enable the availability of your amine for nucleophilic reaction.
The second method is more productive from my experience. However, every organic reaction is unique and doesn't behave ideally for all cases and exceptions do occur. Only after trying can one ascertain with conviction that the method is successful.
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