Reaktion #50539

Reaktionsgleichung

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

Ausbeute 46.6%

Lösungsmittel

Ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe solvent removed under reduced pressure
2. 2
   Sonstigethe residue partitioned between methylene chloride/water
3. 3
   FiltrationThe mixture was filtered
4. 4
   Sonstigethe organic layer separated
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated
8. 8
   SonstigeThe residue was flash-chromatographed on silica gel
9. 9
   Wascheneluting with ethyl acetate/methanol/ammonia (97/3/0.5)

Vorschrift

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.

Quelle