Trifluoroacetic acid → HCID 59756883, compound

Participants

Reaction Steps

tert-Butyl 1-((6,7-dimethoxyquinolin-4-yl)methyl)piperidin-4-ylcarbamate (1 g, 2.49 nmol) was dissolved in DCM (25 mL). While stirring, TFA (1.9 mL, 25 mmol) was added dropwise at rt, and the reaction was allowed to stir for 15 hours. The solvent was removed and the crude compound was taken up in EtOAc (150 mL) and washed with sat. sodium bicarbonate (20 mL). The organics were washed with brine, dried with sodium sulfate, and concentrated. The mixture was columned using 100% DCM to 7% MeOH to give the desired product 1-((6,7-dimethoxyquinolin-4-yl)methyl)piperidin-4-amine (0.54 g, 1.79 mmol, 72% yield). MS (ESI pos. ion) m/z: 302.2 (MH+). Calc'd exact mass for C17H23N3O2: 301. 1HNMR (400 MHz, CDCl3): 8.63-8.64 (d, J=4.4 Hz, 1H), 7.63 (s, 1H), 7.41 (s, 1H), 7.22-7.23 (d, J=4.4 Hz, 1H), 4.03 (s, 3H), 4.01 (s, 3H), 3.83 (s, 2H), 2.84-2.87 (bd, J=12.0 Hz, 2H), 2.70-2.73 (m, 1H), 2.11-2.16 (bt, J=11.2 Hz, 2H), 1.78-1.82 (bd, J=12.8 Hz, 2 H), 1.37-1.41 (m, 2H).

Provenance & Evidence