Acryloyl chloride → 1-(4-Methylpiperazin-1-yl)prop-2-en-1-one

Participants

Reaction Steps

A dry round-bottom flask was charged with 1-methylpiperazine (0.15 mL, 1.36 mmol), diisopropylethylamine (0.65 mL, 3.72 mmol) and CH2Cl2 (6 mL) and then the solution was cooled with an ice-water bath. Acryloyl chloride (0.10 mL, 1.24 mmol) was then added dropwise and the reaction was allowed to warm to room temperature. After 3 hours TLC indicated reaction completion. The CH2Cl2 was removed and the residue taken up in EtOAc, washed with NaHCO3 (sat.) (1×), brine (2×) and then dried over MgSO4. The EtOAc was removed in vacuo which yielded after drying, the title compound as an orange-brown oil. (400 MHz, CDCl3) 6.57 (dd, J1=16.8 Hz, J2=10.5 Hz, 1H), 6.29 (d, J=16.8 Hz, 1H), 5.70 (d, J=10.5 Hz, 1H), 3.73 (bs, 2H), 3.60 (bs, 2H), 2.46-2.41 (m, 4H), 2.34 (s, 3H); MS ESI 155.0 [M+H]+, calcd for [C8H14N2O+H]+

Provenance & Evidence