Hydrochloric Acid → 2-{4-[(methylamino)methyl]-2-phenyl-1H-imidazol-1-yl}-2-phenylethanol dihydrochloride

To a solution of methyl (4-formyl-2-phenyl-1H-imidazol-1-yl)(phenyl)acetate (200 mg) in methanol (10 mL) was added 40% methylamine methanol solution (243 mg) and the mixture was stirred for 15 min. Sodium borohydride (71 mg) was added and the mixture was stirred for 30 min. 1 mol/L Hydrochloric acid was added to the reaction mixture and the mixture was stirred for 5 min. The mixture was neutralized with saturated sodium hydrogen carbonate solution, and extracted with ethyl acetate-tetrahydrofuran (1:1). The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent:ethyl acetate-methanol=1:0→3:2) and dissolved in methanol (5 mL). A 4 mol/L hydrogen chloride-ethyl acetate solution (1 mL) was added, and the mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue, and insoluble materials were collected by filtration to give the title compound as a colorless powder (yield 63 mg, yield 27%).

1. stirringthe mixture was stirred for 30 min
2. stirringthe mixture was stirred for 5 min
3. extractionextracted with ethyl acetate-tetrahydrofuran (1:1)
4. dry with materialThe extract was dried over anhydrous magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by basic silica gel column chromatography (eluent:ethyl acetate-methanol=1:0→3:2)
7. dissolutiondissolved in methanol (5 mL)
8. additionA 4 mol/L hydrogen chloride-ethyl acetate solution (1 mL) was added
9. concentrationthe mixture was concentrated under reduced pressure
10. additionEthyl acetate was added to the residue, and insoluble materials
11. filtrationwere collected by filtration

ORD record

ord-9a117ab9963e4784b56e18c242b43727

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08334301B2