Potassium Iodide → 1-(3,4,5-Trimethoxybenzoyl)-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepan-1-yl)ethyl)-3-phenylpyrrolidine

Participants

Reaction Steps

Combine 1-(3,4,5-trimethoxybenzoyl)-3-phenyl-3-(2-methanesulfonyloxyethyl)pyrrolidine (prepared from (−)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid salt)(1.83 g, 3.94 mmol), 4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane hydriodic acid salt (2.04 g, 3.75 mmol), potassium iodide ((0.62 g, 3.75 mmol), and triethylamine (1.15 mL, 8.25 mmol) in acetonitrile (54 mL). Heat to reflux. After 43 hours, evaporate in vacuo, dilute the evaporated reaction mixture with dichloromethane, extract with a saturated aqueous sodium bicarbonate solution, water, and then with brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with dichloromaethane, then 10% methanol/dichloromethane to give the title compound.

Provenance & Evidence