# How would 2-(chloromethyl)-1-methylpyrrolidine recyclize into 3-chloro-1-methylpiperidine with only water?

My Attempt

I always get thrown off by mechanisms with just water as a solvent. I've attached my work as far as I could get but I'm not sure where to go from there. Thank you!

• Not sure but after you got the acyclic amine. The nitrogen could attack the $\ce{C-Cl}$ via $\ce{S_N2}$. The liberated $\ce{Cl-}$ would in turn attack the $\ce{H2O+}$. – Avyansh Katiyar Jun 8 '18 at 3:40