Hydrochloric Acid → (R)-2-vinylpiperidine hydrochloride

Participants

Reaction Steps

A solution of HCl (4 N in 1,4-dioxane, 11.1 mL, 47.9 mmol) was added to an ice bath cooled reaction vessel containing (R)-tert-butyl 2-vinylpiperidine-1-carboxylate (2.53 gm, 12.0 mmol). The reaction mixture was then stirred at rt for 2 hr. The reaction mixture was concentrated and dried under vacuum to give (R)-2-vinylpiperidine hydrochloride (1.62 gm, 11.0 mmol, 92% yield) as a white solid. 1H NMR (400 MHz, CD3OD) δ ppm 5.89 (1H, ddd, J=17.5, 10.6, 6.6 Hz), 5.50-5.37 (2H, m), 3.74-3.64 (1H, m), 3.38 (1H, d, J=12.6 Hz), 3.09-2.98 (1H, m), 2.04-1.83 (3H, m), 1.74-1.55 (3H, m).

Provenance & Evidence