[Nebula]

Ok this is second year stuff anyways
I have a nitrogen double bonded to a carbon ring and attached to a hydroxide group and I am to treat it with an acid.
The product is a secondary amine where twO substituents are part of a ring. The ring has a -OH group on a carbon next to the nitrogen. From memory.

Can someone give me a hint for the mechanism?
The hydroxyl group can accept a proton thus making it a good leaving group.
When this leaves I get a positively charged nitrogen. Is this allowed?
And will this allow for a c-c bond to break and form a c-n bond?

And if water leaves how do I get a hydroxyl group on the carbon?

Any help welcome,
L