Potassium Iodide → 4-[Bis(4-methoxyphenyl)methyl]-1-[3-(3,4-dimethoxyphenoxy)propyl]piperidine

Participants

Reaction Steps

A mixture of 5.58 g (0.02 mole) of 4-[bis(4-methoxyphenyl)methyl]piperidine, 4.83 g (0.021 mole) of 4-(3-chloropropoxy)-1,2-dimethoxybenzene, and potassium carbonate, 5.52 g (0.04 mole) was heated overnight at reflux in 350 ml of 1-butanol containing potassium iodide (0.3 g). The reaction mixture was stripped to dryness, and the residue partitioned between chloroform-5% sodium hydroxide and chloroform-water. Removal of chloroform gave a dark brown oil. The oil was subjected to column chromatography on a silica gel column with elution via ethyl acetate-dimethoxy ethane. This produced 4.72 g (46.7%) of dark brown oil.

Provenance & Evidence