Are trying to protect a primary or secondary amine? What conditions will your reactant undergo? If it is a secondary it might be possible to protect
it with a benzyl group via Sn2 with benzyl chloride. I don't know how reversible benzyl groups with hydrolysis of amines, but they tend to be willing
to form carbocations and have the double bonds to help push off the positively charged amine salt. Though that is just conjecture for what might be
more available option, because you'd just need benzyl alcohol and HCl to form benzyl chloride. My reasoning for mentioning it is this statement from
benzylamine wikipedia
Quote: |
Benzylamine is used as a masked source of ammonia, since after N-alkylation, the benzyl group can be removed by hydrogenolysis
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So hydrogenolysis would probably work here, but again I don't know if there would be an easier method. |