Benzylamine → HCID 67389904, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(3-(benzylamino)-4-nitrophenyl)piperidine-4-carboxylic acid (0.2 g, 0.56 mmol) and benzylamine (0.06 mL, 0.56 mmol) in DMF (5 mL) was added diisopropylethylamine (0.198 mL, 1.12 mmol) under argon. The mixture cooled to 0° C., HATU (0.212 g, 0.56 mmol) was added at that temperature and then stirred at room temperature for 4 h. After completion of reaction (by TLC), H2O (5 mL) was added drop by drop. The resulting yellow precipitate was filtered, washed with 2 mL of water, dried (high vacuum, 14 h) to furnish N-benzyl-1-(3-(benzylamino)-4-nitrophenyl)piperidine-4-carboxamide (0.21 g), 84% yield. 1H NMR (500 MHz, DMSO): δ 1.51 (m, 2H), 1.74 (m, 2H), 2.48 (m, 1H), 2.96 (m, 2H), 3.93 (m, 2H), 4.26 (d, J=5.9 Hz, 2H), 4.59 (d, J=5.8 Hz, 2H), 5.95 (d, J=2.45 Hz, 1H), 6.42 (dd, J=2.5 Hz, 1H), 7.24 (m, 4H) 7.37 (m, 4H), 7.42 (m, 2H), 7.91 (d, J=9.7 Hz, 1H), 8.35 (m, 1H), 8.84 (m, 1H). HRMS (ESI) calculated for C26H28N4NaO3: 467.2054, Found: 467.2054.

Provenance & Evidence