Hydrochloric Acid → 1-(Tetrahydro-2H-pyran-4-yl)piperidin-4-amine

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Reaction Steps

9.2 g (0.0323 mol, 1 eq) of 1,1-dimethylethyl [1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]carbamate, 65 mL (0.258 mol, 8 eq) of 4 M HCl in dioxane, and enough methanol to achieve dissolution were combined and stirred at ambient temperature overnight. The reaction mixture was then evaporated. Dichloromethane and 1 M NaOH were added. Sodium chloride was then added to saturate the aqueous layer. The aqueous layer was extracted with dichloromethane twice. The organic layers were combined, dried with sodium sulfate, and evaporated to yield 5.5 g (92% yield) of 1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine as a low melting white solid. 1H-NMR (400 MHz, DMSO-d6): δ 3.86 (m, 2H), 3.24 (m, 2H), 2.77 (m, 2H), 2.46 (m, 1H), 2.35 (m, 1H), 2.25-1.05 (v br s, 2H, NH2), 2.07 (m, 2H), 1.64 (m, 4H), 1.39 (m, 2H), 1.16 (m, 2H); MS (ESI): 185 [M+H]+.

Provenance & Evidence