1-(Cyclohex-1-en-1-yl)pyrrolidine is stirred with dilute aqueous $\mathrm{HCl}$. The organic products after the reaction are

Enamine formation is reversible. Protonation at the beta carbon gives the iminium ion, water adds at the C=N+ carbon, and the carbinolamine collapses to cyclohexanone and the amine, which is protonated as pyrrolidinium chloride under the acidic conditions.