Sodium Bicarbonate → 1-Benzoyl-3-[2-[4-(benzothiazol-2-yl)-piperidin-1-yl]-ethyl]-3-(3,4-dimethoxy-phenyl)-pyrrolidine

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Reaction Steps

Combine 1-benzoyl-3-(3,4-dimethoxy-phenyl)-3-(2-methanesulfonyl-ethyl)-pyrrolidine (0.63 g, 1.45 mmol) and 4-(benzothiazol-2-yl)-piperidine (0.35 g, 1.60 mmol), and sodium bicarbonate (0.24 g, 2.9 mmol) in tetrahydrofuran/water (15/4) (30 mL). Heat to reflux. After 48 hours, cool to ambient temperature and evaporate in vacuo to obtain a residue. Partition the residue between dichloromethane and 5% sodium bicarbonate solution. Dry the organic layer over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 5/1 ethyl acetate/methanol to give a solid. Combine the solid with dichloromethane and extract with 5% sodium bicarbonate solution. Dry the organic layer over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Dry the residue in vacuo at 65° C. to give the title compound: Rf=0.24 (silica gel, 5/1 ethyl acetate/methanol); mp; 60-62° C. Elemental Analysis calculated for C33H37N3O3S·0.25 H1O: C 70.75; H 6.75; N 7.50; Found: C 70.79; H 6.70; N 7.39.

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