Reacción #10876

Ecuación de reacción

1-acetyl-4-(4-aminophenyl)piperazine

1-acetyl-4-(4-amino-phenyl)piperazine

thiocarbonyldiimidazole

→

1-(acetyl)-4-(4 isothiocyanatophenyl)piperazine

Rendimiento 84.0%

Disolventes

N,N-dimethylformamide

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Otrothe cooling bath was removed
3. 3
   workup.STIRRINGthe solution was stirred for 1 h
4. 4
   workup.ADDITIONIce-water was added
5. 5
   Extracciónthe mixture was extracted with ether (4×50 mL)
6. 6
   LavadoThe combined ether layers were washed with brine
7. 7
   Secadodried (MgSO4)
8. 8
   Filtraciónfiltered
9. 9
   Otroevaporated

Procedimiento

A solution of 1-acetyl-4-(4-aminophenyl)piperazine (1.0 g, 4.6 mmol) (from Step B above) in N,N-dimethylformamide (10 mL) was added dropwise to a cooled (−15° C.) solution of thiocarbonyldiimidazole (855 mg, 4.8 mmol) in N,N-dimethylformamide (10 mL). After the addition was complete, the mixture was stirred at −15° C. for 30 min, then the cooling bath was removed and the solution was stirred for 1 h. Ice-water was added and the mixture was extracted with ether (4×50 mL). The combined ether layers were washed with brine, dried (MgSO4), filtered, and evaporated to give 1-(acetyl)-4-(4 isothiocyanatophenyl)piperazine (1.0 g, 84%).

Fuente