Acetyl chloride → HCID 18172362, compound

Participants

Reaction Conditions

Reaction Steps

2-(4-Methyl-1-piperazinyl)benzaldehyde (7.8 g, 38 mmol) was dissolved in 0.1% aqueous isopropanol (62 mL) at 20-25° C. under a nitrogen atmosphere and then 2.8 mL (40 mmol) of neat acetyl chloride was slowly added. The resulting slurry was cooled to 0-5° C., granulated for 1 hour, and then filtered. The cake was washed with cold (0-5° C.) isopropanol (8 mL) followed by hexanes (16 mL) and then dried in vacuo at 25-30° C. The title compound (7.9 g, 83% yield) was obtained as a light yellow solid. If desired, the title compound can be recrystallized from refluxing isopropanol (6 L/kg of solid) to afford rod-like crystals (mp 225-226° C.) which were recovered in 93% yield. 1H NMR (CDCl3) δ 12.3 (s, 1H), 10.1 (s, 1H), 7.71 (m, 1H), 7.69 (m, 1H), 7.15 (m, 1H), 7.05 (m, 1H), 3.62 (m, 2H), 3.51 (m 2H), 3.26 (m, 4H), and 2.86 (s, 3H). 13C NMR (CDCl3) δ 191.24, 152.24, 135.70, 134.30, 128.55, 124.03, 119.75, 54.00, 49.94 and 43.74. Anal. Calcd for C12H16N2O HCl: C, 59.87; H, 7.12; N, 11.64. Found: C, 59.98; H, 7.23; N, 11.65.

Provenance & Evidence