Reacción #497520

Ecuación de reacción

1-(4-bromo-benzyl)-3-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-2-ylideneamine

1-(4-chloro-benzyl)-piperazine

potassium t-butoxide

BINAP

→

1-{4-[4-(4-chloro-benzyl)-piperazin-1-yl]-benzyl}-3-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-2-ylideneamine

Rendimiento 18.0%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroNitrogen was bubbled through the suspension for 5 min
2. 2
   TemperaturaAfter this time, the mixture was cooled to rt
3. 3
   Filtraciónfiltered
4. 4
   LavadoThe collected solids were washed with additional toluene
5. 5
   Concentraciónthe combined filtrate and washings were concentrated under reduced pressure
6. 6
   OtroThe crude product was purified by chromatography on silica

Procedimiento

To a solution 1-(4-bromo-benzyl)-3-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-2-ylideneamine (0.25 g, 0.55 mmol) in toluene (20 ml) was added 1-(4-chloro-benzyl)-piperazine (0.16 g, 0.55 mmol), potassium t-butoxide (216 mg, 1.93 mmol), Pd2(dba)3 (35 mg, 0.038 mmol) and BINAP (48 mg, 0.077 mmol). Nitrogen was bubbled through the suspension for 5 min and then the reaction was heated to 105° C. for 24 h. After this time, the mixture was cooled to rt and filtered. The collected solids were washed with additional toluene and then the combined filtrate and washings were concentrated under reduced pressure. The crude product was purified by chromatography on silica to provide 1-{4-[4-(4-chloro-benzyl)-piperazin-1-yl]-benzyl}-3-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-2-ylideneamine (57 mg, 18%). HPLC-MS 584 [M+1]+, 293.

Fuente