Reaktion #74249

Reaktionsgleichung

N1-Trityl-N-(4-methoxyphenyl)benzimidazol-5-amine

THF

lithiumbis(trimethylsilyl)amide

THF

Phenylethylbromide

→

N-(4-Methoxybenzyl)-N-phenethyl-1H-benzo[d]imidazol-5-amine

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate (3×25 ml)
2. 2
   TrocknenThe combined organic layers were dried over Na2SO4
3. 3
   Sonstigeevaporated
4. 4
   workup.DISSOLUTIONThe residue was dissolved in MeOH (5 ml)
5. 5
   workup.ADDITIONtreated with TFA (1 ml)
6. 6
   TemperaturAfter heating
7. 7
   Temperaturto reflux for 1 h the mixture
8. 8
   workup.ADDITIONwas poured into saturated NaHCO3-solution
9. 9
   Extraktionextracted with ethyl acetate (3×25 ml)
10. 10
    TrocknenThe combined organic layers were dried over Na2SO4
11. 11
    Sonstigeevaporated
12. 12
    SonstigeThe residue was purified by flash chromatography on silica using a CHCl3/MeOH gradient
13. 13
    Sonstigert 16.74 min (96.3%)

Vorschrift

N1-Trityl-N-(4-methoxyphenyl)benzimidazol-5-amine (990 mg; 2 mmol; 1 eq.) was dissolved in THF (5 ml), cooled to 0° C. and treated with lithiumbis(trimethylsilyl)amide 1M in THF (2.4 ml; 2.4 mmol; 1.2 eq.). Phenylethylbromide (0.330 ml; 2.4 mmol; 2.4 eq.) was added and the mixture was stirred at room temperature for 24 h. The mixture was diluted with water and extracted with ethyl acetate (3×25 ml). The combined organic layers were dried over Na2SO4 and evaporated. The residue was dissolved in MeOH (5 ml) and treated with TFA (1 ml). After heating to reflux for 1 h the mixture was poured into saturated NaHCO3-solution and extracted with ethyl acetate (3×25 ml). The combined organic layers were dried over Na2SO4 and evaporated. The residue was purified by flash chromatography on silica using a CHCl3/MeOH gradient. Yield: 0.058 g (8.1%); MS m/z: 358.1 [M+H]+; 1H-NMR (500 MHz, DMSO d6): δ 2.85 (t, 2H, 3J=7.9 Hz); 3.57 (t, 2H, 3J=7.9 Hz); 3.69 (s, 3H); 4.44 (s, 2H); 6.77-6.79 (m, 2H); 6.83-6.86 (m, 2H); 7.14-7.16 (m, 2H); 7.18-7.21 (m, 1H); 7.23-7.25 (m, 2H); 7.28-7.30 (m, 2H); 7.38-7.39 (m, 1H); 7.92 (s, 1H); 11.92 (br s, 1H); HPLC (METHOD [A]): rt 16.74 min (96.3%)

Quelle