Isopropanol → HCID 9820230, compound

Participants

Reaction Steps

A mixture of 0.4 g of 3-{2-[3-(3-benzyl-8-aza-bicyclo[3.2.1]oct-8-yl)-propyl]-benzimidazol-1-yl }-propionitrile, 20 mL of isopropanol and 2 mL of 0.4M sodium in isopiopanol was heated to reflux for 2 h. Conversion was complete by TLC (80:20:1 ethyl acetate:methanol:triethylamine). The mixture was cooled, diluted with 10 mL of saturated sodium bicarbonate and concentrated. The residue was partitioned between 3×100 mL of chloroform and 50 mL of water. After drying over magnesium sulfate and concentration under reduced pressure, the residue was purified by preparative TLC eluting with 400:100:25 ethyl acetate:methanol:triethylamine. The major band (UV visualization) was 2-[3-(3-benzyl-8-aza-bicyclo[3.2.1]oct-8-yl)-propyl]-1H-benzimidazole (258 mg): MS (m+1)=362.5; 1H NMR (400 MHz, CDCl3) 7.58 (d, 1H), 7.52 (d, 1H), 7.6-7.2 (complex, 7H), 3.38 (s, 2H), 3.18 (m, 2H), 2.82 (m, 2H), 2.6 (m, 2H), 2.22 (m, 2H), 2.1 (m, 2H), 1.85 (m, 5H), 1.6 (m, 2H).

Provenance & Evidence