1-Methylpiperazine → 3-Chloro-6-(4-methylpiperazin-1-yl)pyridazine

Participants

Reaction Conditions

Reaction Steps

A 25-mL single-neck round bottomed flask equipped with a magnetic stirrer was purged with nitrogen and charged with 3,6-dichloropyridazine (1.49 g, 10.0 mmol) and N-methylpiperazine (1.17 g, 11.7 mmol), and the flask was placed in an oil bath, which was heated to 100° C. After 1.5 h the flask was cooled to room temperature, and the resulting cake was crushed and triturated with acetonitrile (10 mL). The suspension was filtered, and the filter cake was mixed with 10% aqueous potassium carbonate (15 mL). The resulting mixture was extracted with MtBE (2×35 mL). The organic extracts were combined, dried over sodium sulfate and filtered. The filtrate was evaporated under reduced pressure to afford a 60% yield (1.27 g) of 122e as a white solid: mp 106-107° C.; 1H NMR (300 MHz, CDCl3) δ 7.20 (d, 1H, J=9.5 Hz), 6.89 (d, 1H, J=9.6 Hz), 3.65 (t, 4H, J=5.1 Hz), 2.53 (t, 4H, J=5.1 Hz), 2.35 (s, 3H); MS (ESI+) m/z 213.1 (M+H).

Provenance & Evidence