Morpholine → HCID 58765296, compound

Participants

Reaction Steps

Zinc chloride (21 mg, 0.15 mmol) and morpholine (40 μL, 0.46 mmol) were added to methyl 13-cyclohexyl-6,7-dihydro-6-oxo-5H-indolo[2,1-a][2]benzazepine-10-carboxylate (30 mg, 0.078 mmol) in MeOH (3 mL). The mixture was heated at 60° C. for 3 hr when sodium cyanoborohydride (29 mg, 0.46 mmol) was added. Heating was continued for another hr. The mixture was concentrated and the crude product purified by chromatography on a SiO2 preparative plate using dichloromethane containing 2 N methanolic ammonia (100:1). to afford the product as a light yellow solid (25 mg, 70%). ESI-MS m/z 806 (MH+); 1H NMR (500 MHz, MeOD) δ 1.28-1.36 (m, 1 H) 1.36-1.53 (m, 2 H) 1.59-1.71 (m, 1 H) 1.74-1.86 (m, 2H) 1.92-2.19 (m, 4 H) 2.36-2.53 (m, 1 H) 2.58 (m, 1 H) 2.73 (m, 2 H) 2.89 (m, 1 H) 2.99 (m, 1 H) 3.12 (m, 1 H) 3.38 (m, 1 H) 3.58-3.77 (m, 4 H) 3.86-4.00 (m, 3 H) 4.04-4.17 (m, 1 H) 4.51-4.66 (m, 1 H) 7.35-7.50 (m, 4 H) 7.71 (d, J=8.55 Hz, 1 H) 7.88 (m, 1 H) 8.13 (m, 1 H).

Provenance & Evidence