Triethylamine → HCID 30288965, compound

Participants

Reaction Steps

A solution of oxalyl chloride (4.19 g, 33.0 mmol) in dichloromethane (12.5 ml) was added dropwise at room temperature to a solution of 3-chlorocinnamic acid (5.48 g, 30.0 mmol) and N,N-dimethylformamide (2 drops) in dichloromethane (240 ml). After 2 h the solution was evaporated and the residue redissolved in dichloromethane (160 ml), then a solution of piperazin-2-one (2.70 g, 27 mmol) and triethylamine (6.07 g, 60.0 mmol) in dichloromethane (80 ml) was added dropwise at 0° C. The reaction mixture was allowed to reach room temperature over 16 h, then poured onto 10% aq. potassium hydrogensulfate solution. The organic layer was washed with sat. aq. sodium hydrogencarbonate solution and 10% aq. sodium chloride solution, dried, and evaporated to produce the title compound (5.12 g, 72%). Yellow solid, MS (EI)=264.1 (M)+.

Provenance & Evidence