Toluene → 1255204-84-2

Participants

Reaction Conditions

Reaction Steps

Piperazine (4.51 g, 52.4 mmol) and 4-methyl-5-[(2R)-oxiran-2-yl]-2-benzofuran-1(3H)-one (20.0 g, 105 mmol) were charged to a 3-neck 500-mL roundbottom flask, equipped with a reflux condenser, under nitrogen. Toluene (80.0 mL, 751 mmol) and N,N-dimethylacetamide (80 mL, 854 mmol) were added to provide a suspension. The reaction mixture was warmed to 110° C., becoming homogeneous at 25° C. After stirring for 4.5 h at 110° C., the temperature was increased to 115° C. to drive the reaction forward. After stirring for 48 h, the reaction mixture was cooled to RT. On cooling, crystallization occurred. Water was added via addition funnel (45 mL), generating a thick slurry. The suspension was filtered and the solids were washed with 4:1 water:DMA (60 mL), followed by water (2×35 mL). The solid was dried on the funnel under vacuum with a nitrogen sweep to constant mass. 5,5′-{Piperazine-1,4-diylbis[(1R)-1-hydroxyethane-2,1-diyl]}bis(4-methyl-2-benzofuran-1(3H)-one) was isolated. 1H-NMR (500 MHz, CDCl3) δ ppm 7.80 (s, 4H), 5.25 (s, 4H), 5.11 (d, J=11 Hz, 2H), 4.30-3.51 (broad, 2H), 2.90 (broad, 4H), 2.69-2.50 (m, 6H), 2.44 (t, J=11 Hz, 2H), 2.30 (s, 6H).

Provenance & Evidence