4-Aminotetrahydropyran hydrochloride

A mixture of 4-(hydroxyimino)-3,5,6-trihydro-2H-pyran (43.4 mmol) and Raney Nickel (200 mg) in ethanol was hydrogenated (90 psi) at room temperature for 3 days. The mixture was filtered through a pad of Celite, washed with MeOH, and concentrated. The residue was dissolved in MeOH, treated with HCl (4 N in dioxane, 60 mmol), and concentrated to give perhydro-2H-pyran-4-ylamine hydrochloride (4-Aminotetrahydropyran hydrochloride).