Indoline → HCID 178523688, compound

Participants

Reaction Steps

To a stirred mixture of N-trans-4-[2-(4-Benzo[1,3]dioxol-4-yl-piperazin-1-yl)-ethyl]-cyclohexylamine hydrochloride (Intermediate A) (31.1 mg, 85 μmol) in DCM (1 ml) at room temperature N,N-diisopropylethylamine (110 mg, 148 μl, 850 μmol, Eq: 10) and triphosgene (27.7 mg, 93.5 μmol, Eq: 1.1) was added carefully and the solution stirred for minutes at room temperature. Indoline (12.2 mg, 102 μmol, Eq: 1.2) was added and stirred for 30 minutes at room temperature. The reaction mixture was quenched with 10 mL sat NaHCO3 and extracted with DCM (3×15 mL). The organic layers were dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 100 g, 0% to 10% MeOH in DCM) to yield the title compound as an white solid (27.6 mg, 68.1%), MS (ISP) m/z=477.2 [(M+H)+].

Provenance & Evidence