Diisopropylethylamine → 1-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1-(4-fluorobenzyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-dichlorophenyl)piperidine

Participants

Reaction Steps

Combine 1-(3,4,5-trimethoxybenzoyl)-3-(3,4-dichlorophenyl)-3-(2-methanesulfonyloxyethyl)piperidine (1.14 mmol) and (1-(4-fluorobenzyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine (0.56 g, 1.7 mmol), and N,N-diisopropylethylamine (0.50 g) in acetonitrile (12 mL). Heat to reflux. After 2 days, partition the residue between ethyl acetate and water. Separate the organic layer and extract twice with saturated aqueous sodium bicarbonate solution and brine. Dry the organic layer over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 30/70/0.33 methanol/ethyl acetate/concentrated aqueous ammonia to give the title compound: Rf=0.50 (silica gel, 30% methanol/ethyl acetate).

Provenance & Evidence