Water → Tert-butyl 4-(benzo[d][1,3]dioxol-4-yl)piperazine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Tert-butyl piperazine-1-carboxylate (1.11 g, 5.97 mmol) was added to a solution of 4-bromobenzo[d][1,3]dioxole (1 g, 4.97 mmol) in Toluene (15.0 ml). The resulting suspension was degassed using a stream of argon. Cesium carbonate (2.27 g, 558 μl, 6.96 mmol), racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphtyl (232 mg, 373 μmol, Eq: 0.075) and Palladium (II) Acetate (55.8 mg, 249 μmol) were added to this mixture. The reaction was then heated at 100° C. over night. The reaction was cooled to rt, 40 ml of water was added and the mixture was extracted with Ethyl Acetate (2×80 ml). The organic layers were dried over MgSO4 and concentrated under vacuum. The crude material was purified by flash chromatography (silica gel, 50 g, 0% to 50% EtOAc in heptane). to yield tert-butyl 4-(benzo[d][1,3]dioxol-4-yl)piperazine-1-carboxylate as a white solid (1.15 g, 75%). MS (ISP) m/z=307.4 [(M+H)+].

Provenance & Evidence