1,4-Dichlorophthalazine → Phthalazine

Participants

Reaction Steps

1,4-dichlorophthalazine (1.6 g, 8 mmol) was slurried in 80 mL of MIBK and 2,6 cis-dimethyl piperazine (3.6 g, 32 mmol, 4 eq) was added. The reaction was stirred overnight and the solvent was removed in vacuo. The crude material was dissolved in 200 mL of CH2Cl2 and washed with 1×30 mL of a 1:1 mixture of H2O and sat. sodium bicarbonate and 1×30 mL of sat. NaCl solution. The organic layer was dried over MgSO4, filtered, and concentrated. Purification by column chromatography (100:5:1 dichloromethane:methanol:triethylamine) afforded 1.6 g (72%) of 1-chloro-4-(cis)-3,5-dimethylpiperazin-1-yl)phthalazine. MS (M+H)+=277.1.

Provenance & Evidence