Reacción #10888

Ecuación de reacción

4-[4-(1-cyclopentyl)-1-piperazinyl]benzenamine

4-(4-cyclopentyl-1-piperazinyl)benzenamine

thiocarbonyldiimidazole

→

4-cyclopentyl-1-(4 isothiocyanatophenyl)piperazine

Rendimiento 93.2%

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 hr
4. 4
   workup.ADDITIONthen poured into ice-water (1500 mL)
5. 5
   workup.STIRRINGstirred for 30 min.
6. 6
   Filtraciónthe precipitate filtered
7. 7
   Lavadowashed with water
8. 8
   Otrodried under vacuum

Procedimiento

A solution of 4-[4-(1-cyclopentyl)-1-piperazinyl]benzenamine (5.7 g, 22.4 mmol) (from Step B above) in N,N-dimethylformamide (75 mL) was added dropwise over 20 min to a cooled (−15° C.) solution of thiocarbonyldiimidazole (4 g, 22.5 mmol) (Aldrich) in N,N-dimethylformamide (40 mL). After the addition was complete, the mixture was stirred at −15° C. for 20 min, then the cooling bath was removed and the solution was stirred for 1 hr. then poured into ice-water (1500 mL), stirred for 30 min. then the precipitate filtered and washed with water and dried under vacuum to give 4-cyclopentyl-1-(4 isothiocyanatophenyl)piperazine (6 g, 93%)

Fuente