m-Chloroperbenzoic acid → HCID 6481412, compound

Participants

Reaction Steps

NaHMDS (1.3 mL of a 1.0 M in THF solution, 1.3 mmol) was added to a stirring solution of 1H-indole-4-carboxylic acid methyl ester (0.048 g, 0.27 mmol) and (4-benzoyl-piperazin-1-yl)-acetonitrile (63 mmol, 0.27 mmol) in THF (3 mL) and the reaction mixture was stirred overnight. mCPBA (0.01 g of 77% max., 0.43 mmol) was added to the reaction mixture, stirred 1 d, and the solution was partitioned between brine (15 mL) and EtOAc (3×10 mL). The combined organic layers were dried (MgSO4), filtered, concentrated and purified using Shimadzu automated preparative HPLC System to give 1-(4-benzoyl-piperazin-1-yl)-2-(1H-indol-4-yl)-ethane-1,2-dione (0.028 mg, 77 mmol, 29%) as a yellow solid: MS m/z: (M+H)+ calcd for C21H19N3O3:362.14; found 362.09. HPLC retention time: 1.13 minutes (column A).

Provenance & Evidence