4-Phenylbenzylamine → 3-Benzyloxy-1-[(phenylbenzylcarbamoyl)methyl]-2-(1H)-pyridinone

15 (0.5 g, 1.4 mmol) was dissolved in 50 mL of dry CH2Cl2. 4-phenylbenzylamine (0.28 g, 1.5 mmol) was dissolved in 10 mL of dry CH2Cl2 to yield an almost clear, colorless solution and was quickly added to the stirring solution of 15. The reaction flask was protected from light with aluminum foil and stirred at room temperature under a dinitrogen atmosphere for 18 h. A white solid was removed by vacuum filtration. A second crop of white precipitate was isolated after cooling the filtrate at 4° C. for 3 h. The CH2Cl2 filtrate layer was washed with 0.05 M aqueous sodium bicarbonate solution (3×25 mL). The methylene chloride layer was washed with ddH2O (1×25 mL) and then dried over anhydrous sodium sulfate. The clear, colorless solution was concentrated by rotary evaporation to yield a white solid. Yield: 55%. 1H NMR (d6-DMSO, 400 MHz, 25° C.): δ 4.33 (d, J=6.0 Hz, 2H, —CH2—), 4.61 (s, 2H, —CH2—), 5.00 (s, 2H, —CH2—), 6.12 (t, J=7.2 Hz, 1H, Ar—H), 6.91 (d, J=7.6 Hz, 1H, Ar—H), 7.22 (d, J=6.8 Hz, 1H, Ar—H), 7.39 (m, 9H, Phenyl-H, Bz-H), 7.62 (m, 5H, Bz-H), 8.70 (t, J=5.8 Hz, 1H, —NH—).

1. customto yield an almost clear, colorless solution
2. customA white solid was removed by vacuum filtration
3. customA second crop of white precipitate was isolated
4. temperatureafter cooling the filtrate at 4° C. for 3 h
5. washThe CH2Cl2 filtrate layer was washed with 0.05 M aqueous sodium bicarbonate solution (3×25 mL)
6. washThe methylene chloride layer was washed with ddH2O (1×25 mL)
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationThe clear, colorless solution was concentrated by rotary evaporation
9. customto yield a white solid

ORD record

ord-ac48a07098e34ecf9a8ecc98cf871f77

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08008510B2