Nitrogen → (2,6-Dimethoxy-naphthalen-1-yl)-[4-(2-piperidin-1-yl-ethoxy)phenyl]-methanone

Participants

Reaction Conditions

Reaction Steps

In a dry round bottom flask equipped with stir bar, temperature probe and N2 line, dissolve 2,6-dimethoxynaphthalene (1.0 eq) in CH2Cl2 (5 volume equivalents) at ambient temperature. Cool the solution to 0° C. in with an ice bath, and add 4-(2-piperidin-1-yl-ethoxy)-benzoyl chloride (1.1 eq). Add aluminum chloride (2.0 eq). Once the reaction is determined to be complete, quench the reaction slowly with 1 N NaOH and dilute with additional water and CH2Cl2. Wash the aqueous layer with (1×20 mL) of CH2Cl2. Combine the organic extracts and wash with brine and dry (Na2SO4). Recrystallize the crude product from methanol to give (2,6-dimethoxy-naphthalen-1-yl)[4(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (average yield 68%).

Provenance & Evidence