반응 #50539

반응 방정식

1,5-dimethyl-4-formyl-2-(4-trifluoromethylphenyl)imidazole

Sodium hydroxide

Sodium cyanoborohydride

1-(2,3,4-trimethoxyphenylmethyl)piperazine

→

1-(2,3,4-trimethoxyphenyl)methyl-4-[(2-(4-trifluoromethylphenyl)-1,5-dimethylimidazol-4-yl)methyl]piperazine

수율 46.6%

용매

Ethanol

반응 조건

후처리

1. 1
   기타the solvent removed under reduced pressure
2. 2
   기타the residue partitioned between methylene chloride/water
3. 3
   여과The mixture was filtered
4. 4
   기타the organic layer separated
5. 5
   건조dried over anhydrous magnesium sulfate
6. 6
   여과filtered
7. 7
   기타evaporated
8. 8
   기타The residue was flash-chromatographed on silica gel
9. 9
   세척eluting with ethyl acetate/methanol/ammonia (97/3/0.5)

실험 절차

A solution of 1,5-dimethyl-4-formyl-2-(4-trifluoromethylphenyl)imidazole (0.5 g), 1-(2,3,4-trimethoxyphenylmethyl)piperazine (0.54 g), and titanium(IV)isopropoxide (0.73 g) was allowed to stand for 1 hour at room temperature. Ethanol (10 ml) was added, and the resultant solution was stirred for 1 hour. Sodium cyanoborohydride (90 mg) was then added, and the mixture stirred overnight. Sodium hydroxide was then added until the pH was just over 7, the solvent removed under reduced pressure, and the residue partitioned between methylene chloride/water. The mixture was filtered, the organic layer separated, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was flash-chromatographed on silica gel, eluting with ethyl acetate/methanol/ammonia (97/3/0.5), to yield 0.45 g of 1-(2,3,4-trimethoxyphenyl)methyl-4-[(2-(4-trifluoromethylphenyl)-1,5-dimethylimidazol-4-yl)methyl]piperazine. Treatment with anhydrous hydrochloric acid in ethanol converted the base to its dihydrochloride salt, m.p. 235° C.

출처