1-[3-(4-Iodophenoxy)propyl]piperidine → 1'-[4-(3-piperidin-1-ylpropoxy)phenyl]-3H-spiro[2-benzofuran-1,4'-piperidine]

Participants

Reaction Steps

3H-spiro[2-benzofuran-1,4′-piperidine] (131 mg, 0.695 mmol), 1-[3-(4-iodophenoxy)propyl]piperidine (200 mg, 0.58 mmol) prepared in Reference Example (2), sodium tert-butoxide (78 mg, 0.812 mmol), Pd2(dba)3 (5 mg, 0.0058 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (7 mg, 0.0116 mmol) were mixed, and stirred overnight in 1,4-dioxane in a nitrogen atmosphere at 60° C. The reaction solution was filtered under suction through Celite, diluted with ethyl acetate, washed with water and saturated saline in that order, and the organic layer was dried with sodium sulfate. The solvent was evaporated off under reduced pressure, and the resulting residue was purified through preparative thin-layer chromatography (eluate: chloroform/methanol=10/1) to obtain the entitled compound as a colorless solid (60.5 mg, 26%).

Provenance & Evidence