N,N'-Dimethylethylenediamine → cis-1-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-piperazin-2-one

Participants

Reaction Conditions

Reaction Steps

cis-(5-Bromo-thiophen-3-yl)-(octahydro-quinolin-1-yl)-methanone (0.05 g, 0.15 mmol) was dissolved in DME (1 mL) and piperazin-2-one (0.3 mmol), potassium carbonate (0.15 mmol), copper (I) iodide (0.003 g) and dimethylethylenediamine (0.0013 g) were added. The mixture was heated to 120° C. for 65 hours. The mixture was diluted with DCM (10 mL) and the organic solution washed with water, then evaporated to give a brown oil. The residue was purified by flash chromatography on silica, eluting with 0-40% methanol in DCM. The fractions containing the desired product were combined and evaporated to give the title compound as a pale brown oil (0.032 g). LCMS m/z 348.05 [M+H]+ RT=6.24 min (Analytical Method 2). 1H NMR δ (ppm)(CHCl3-d): 7.0 (s, 1H), 6.7 (s, 1H), 4.6 (m, 1H), 4.0-3.6 (m, 5H), 3.3 (m, 2H), 3.0 (m, 1H), 2.0-1.0 (m, 16H).

Provenance & Evidence