Reaction #70481

Reaction equation

6-piperazin-1-yl-nicotinonitrile

1,4-dichlorophthalazine

Et3N

NMP

→

title compound

Yield 51.1%

6-[4-(4-Chloro-phthalazin-1-yl)-piperazin-1-yl]-nicotinonitrile

Yield 51.1%

Solvents

H2O

Conditions

Workup

1. 1
   TemperatureUpon cooling to room temperature
2. 2
   Otherthe precipitate isolated by filtration
3. 3
   Washrinsing with additional H2O
4. 4
   OtherCrude material is purified by recrystallization (CH2Cl2:heptanes)

Procedure

To a 100-mL round-bottom flask is added 6-piperazin-1-yl-nicotinonitrile (9.60 g, 50 mmol), 1,4-dichlorophthalazine (11.2 g, 55.1 mmol, 1.1 eq), Et3N (3.5 mL, 250 mmol, 5 eq.), and NMP (100 mL). The mixture is heated to 80° C. for 2.5 h. Upon cooling to room temperature, the reaction is poured into H2O (500 mL) and the precipitate isolated by filtration, rinsing with additional H2O. Crude material is purified by recrystallization (CH2Cl2:heptanes) to afford 8.96 g title compound as a beige solid.

Source