Triethylamine → tert-Butyl 4-(4-(ethoxycarbonyl)phenoxy)piperidine-1-carboxylate

Participants

Reaction Steps

648 mg (2.15 mmol) of t-butyl [2-(1-aminoisoquinoline-7-yloxy)ethyl]carbamate was dissolved in a mixture of 2.5 ml of 4 N solution of hydrogen chloride in dioxane and 5 ml of dioxane. The obtained solution was stirred at room temperature overnight. The solvent was evaporated, and the residue was dissolved in 10 ml of DMF. 752 mg (2.36 mmol) of 4-(1-t-butoxycarbonyl-4-piperidyloxy)benzoic acid, 451 mg (2.36 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 319 mg (2.36 mmol) of 1-hydroxybenzotriazole and 0.99 ml (7.08 mmol) of triethylamine were added to the obtained solution, and they were stirred at room temperature overnight. The reaction mixture was treated with dichloromethane as the extracting solvent in an ordinary manner, and the obtained crude product was dissolved in a mixture of 2 ml of 4 N solution of hydrogen chloride in dioxane and 1 ml of dioxane. The obtained solution was stirred at room temperature overnight. The title compound was obtained in the same manner as that in step 4 in Example 1.

Provenance & Evidence