反応 #50539

反応方程式

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

収率 46.6%

溶媒

Ethanol

反応条件

後処理

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

実験手順

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.

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