Cesium carbonate → HCID 59756879, compound

Participants

Reaction Conditions

Reaction Steps

4-(Chloromethyl)-6,7-dimethoxyquinoline hydrochloride (0.75 g, 2.74 mmol), tert-butyl piperidin-4-ylcarbamate (0.77 g, 3.84 mmol), and cesium carbonate (2.68 g, 8.23 mmol) were dissolved in DMF (14 mL) and heated to 80° C. while stirring. After 4 hours, the reaction was cooled, DMF was removed, and the compound was taken up in DCM (150 mL) and water (20 mL). The aqueous layer was extracted 2× with DCM (50 mL). The organics were washed with brine, dried with sodium sulfate, and concentrated to give the desired product tert-butyl 1-((6,7-dimethoxyquinolin-4-yl)methyl)piperidin-4-ylcarbamate (1.04 g, 2.60 mmol, 95% yield). MS (ESI pos. ion) m/z: 402.2 (MH+). Calc'd exact mass for C22H31N3O4: 401. 1HNMR (400 MHz, CDCl3): 8.64-8.65 (d, J=4.4 Hz, 1H), 7.58 (s, 1H), 7.42 (s, 1H), 7.23-7.24 (d, J=4.4 Hz, 1H), 4.57-4.59 (m, 1H), 4.03 (s, 3H), 4.01 (s, 3H), 3.83 (s, 2H), 2.82-2.85 (bd, J=11.6 Hz, 2H), 2.18-2.24 (bt, J=10.8 Hz, 2H), 1.92-1.95 (bd, J=12.4 Hz, 2H), 1.44 (s, 9H), 1.41-1.44 (m, 2H, overlapping).

Provenance & Evidence