Piperidine → HCID 59577773, compound

Participants

Reaction Steps

To a suspension of 6-(benzothiazol-2-yloxy)-1H-indole-2-carbaldehyde (47 mg, 0.16 mmol) in DCM (3 mL) was added piperidine (0.14 mL, 0.12 g, 0.48 mmol), Na(OAc)3BH (51 mg, 0.24 mmol) and the reaction mixture was stirred (rt, 12 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):DCM (0-8%) to provide the title compound as a yellow solid (18 mg, 31%). MS (ESI): mass calcd. for C21H21N3OS, 363.1; m/z found, 364.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.80 (s, 1H), 7.76-7.71 (m, 1H), 7.62 (dd, J=7.9, 0.7, 1H), 7.54 (d, J=8.5, 1H), 7.41-7.33 (m, 1H), 7.30 (d, J=2.0, 1H), 7.25-7.20 (m, 1H), 7.04 (dd, J=8.5, 2.2, 1H), 6.34 (d, J=1.0, 1H), 3.61 (s, J=5.4, 2H), 2.62-2.26 (m, 4H), 1.72-1.53 (m, J=10.9, 5.6, 4H), 1.54-1.30 (m, J=5.1, 2H).

Provenance & Evidence