Reaktion #45984

Reaktionsgleichung

N,N-diethyl-N-[3-(4-nitrophenoxy)propyl]amine

DMF

1-[4-(benzyloxy)phenyl]-2-bromoethanone

→

desired product

[3-(4-{4-[4-(adamantan-1-ylmethoxy)-phenyl]-2-isobutyl-imidazol-1-yl}-phenoxy)-propyl]-diethyl-amine

Lösungsmittel

H2O

Et2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe combined organic layers were washed with brine
2. 2
   Trocknendried over sodium sulfate
3. 3
   SonstigeEvaporation of solvent in vacuuo

Vorschrift

To a stirred solution of N,N-diethyl-N-[3-(4-nitrophenoxy)propyl]amine (1.0 eq., 2.5 mmol) in anhydrous DMF (20 mL) DIEA (3 eq) was added, followed by slow addition of the 1-[4-(benzyloxy)phenyl]-2-bromoethanone (2.5 mmol). The reaction mixture was stirred under nitrogen at rt until completion, as indicated by HPLC. The reaction mixture was then diluted with cold H2O and the product was isolated in Et2O. The combined organic layers were washed with brine and dried over sodium sulfate. Evaporation of solvent in vacuuo afforded the desired product. The crude alkylated aniline was purified by chromatography (Silica gel). Pure product was obtained from 2-7% MeOH/DCM (yield˜30%).

Quelle