2-Chloroethanol → 3-Chloro-N-[1-(2-chlorophenyl)-2-[1-(2-hydroxyethyl)-piperidin-4-ylmethoxy]ethyl]-1H-indole-6-carboxamide

Participants

Reaction Steps

To a solution of 3-chloro-N-[1-(2-chlorophenyl)-2-(piperidin-4-ylmethoxy)ethyl]-1H-indole-6-carboxamide (200 mg, 0.45 mmol) in 5 mL of EtOH was added potassium carbonate (247 mg, 1.8 mmol), potassium iodide (224 mg, 1.4 mmol) and 2-chloroethanol (0.09 mL, 1.4 mmol). The reaction was allowed to stir at room temperature overnight after which time water was added and the resulting precipitate was isolated by filtration. Purification of the filtrate (SiO2: 10:0.5 EtOAc:isopropylamine) provided 70 mg (32%) of the title compound.

Provenance & Evidence