Hydrochloric Acid → 4-(1-(2-pyrrolidin-1-yl-ethyl)-4-(tetrahydro-pyran-4-yl)-1H-imidazol-2-yl)-piperidine

Participants

Reaction Conditions

Reaction Steps

Add aqueous 35% hydrochloric acid (23.20 mL, 4.7 eq) to a solution of tert-butyl 4-[1-(2-pyrrolidin-1-ylethyl)-4-tetrahydropyran-4-yl-imidazol-2-yl]piperidine-1-carboxylate (29.0 g, 60.33 mmol) in isopropyl alcohol (120 mL). Stir at 50° C. for six hours. Concentrate in vacuo. Add water (1 L) and 2 M aqueous sodium hydroxide to adjust the pH to 12. Extract with ethyl acetate (3×200 mL) and dichloromethane (3×200 mL). Dry the organics over anhydrous magnesium sulfate and concentrate in vacuo to give 4-(4-(tetrahydro-2H-pyran-4-yl)-1-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazol-2-yl)piperidine (21.5 g, 100%). MS (ES) m/z=333 [M]+.

Provenance & Evidence