تفاعل #45984

معادلة التفاعل

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

المذيبات

H2O

Et2O

ظروف التفاعل

المعالجة

1. 1
   غسيلThe combined organic layers were washed with brine
2. 2
   تجفيفdried over sodium sulfate
3. 3
   أخرىEvaporation of solvent in vacuuo

الإجراء التجريبي

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%).

المصدر