Piperidine → HCID 49832492, compound

Participants

Reaction Steps

To a suspension of 5-(benzothiazol-2-yloxy)-1-ethyl-1H-indole-2-carbaldehyde (100 mg, 0.3 mmol) in DCE (3 mL) was added piperidine (0.06 mL, 51 mg, 0.62 mmol), Na(OAc)3BH (131 mg, 0.62 mmol) and the reaction mixture was stirred (rt, 60 h). The reaction mixture was partitioned between saturated NaHCO3 (10 ml) and DCM (20 mL). The organic layer was separated and the aqueous layer was extracted with DCM (2×25 mL). The organic layer was dried, filtered and concentrated in vacuo. The resulting residue was purified by silica gel flash chromatography using MeOH (0.2 M NH3):DCM (0-8%) to provide the title compound as a yellow solid (82 mg, 68%). MS (ESI): mass calcd. for C23H25N3OS, 391.2; m/z found, 392.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.73 (d, J=8.1, 1H), 7.59 (d, J=7.9, 1H), 7.49 (d, J=2.3, 1H), 7.39-7.29 (m, 2H), 7.23 (d, J=13.2, 1H), 7.12 (dd, J=8.8, 2.4, 1H), 6.35 (s, 1H), 4.36-4.21 (m, 2H), 3.56 (s, 2H), 2.49-2.25 (m, 4H), 1.54 (d, J=5.3, 4H), 1.51-1.32 (m, 5H).

Provenance & Evidence