反应 #50539

反应方程式

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

收率 46.6%

溶剂

Ethanol

反应条件

后处理

1. 1
   其他the solvent removed under reduced pressure
2. 2
   其他the residue partitioned between methylene chloride/water
3. 3
   过滤The mixture was filtered
4. 4
   其他the organic layer separated
5. 5
   干燥dried over anhydrous magnesium sulfate
6. 6
   过滤filtered
7. 7
   其他evaporated
8. 8
   其他The residue was flash-chromatographed on silica gel
9. 9
   洗涤eluting with ethyl acetate/methanol/ammonia (97/3/0.5)

实验过程

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.

来源