Hydrazine hydrate (1:1) → N-(2-aminoethyl)-N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amine
Reaction equation
[CH2:1]([N:3]([CH2:14][CH2:15][N:16]1C(=O)C2=CC=CC=C2C1=O)[CH2:4][CH2:5][O:6][C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=1)[CH3:2].O.NN>C(O)C>[NH2:16][CH2:15][CH2:14][N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][O:6][C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=1Participants
4
Procedure
To a solution of compound 4 (1.50 g, 4.20 mmol) in ethanol (135 mL) was added hydrazine monohydrate (2.04 mL, 42.0 mmol). The mixture was stirred at room temperature for 14 h. The precipitate was filtered and then washed with ethanol (2×10 mL). The filtrate was evaporated under vacuum and the residue was chromatographed (Al2O3, CH2Cl2/EtOH, 9/1, v/v) to give compound 5 (949 mg, 4.18 mmol) as a yellow oil. Yield 99%; Rf (Al2O3, CH2Cl2/EtOH, 9/1, v/v) 0.36; IR (CCl4) ν 1120, 1190, 1250, 1283, 1453, 1466, 2700-3000 cm−1; 1H NMR (200 MHz, CDCl3) δ 1.08 (t, 3H, J=7.1 Hz), 1.54 (se, 2H), 2.67 (m, 6H), 2.94 (t, 2H, J=6.0 Hz), 4.12 (t, 2H, J=6.0 Hz), 7.13 (ddd, 1H, 5JH-F=0.9 Hz, J=4.8, 7.9 Hz), 7.32 (ddd, 1H, 4JH-F=10.1 Hz, J=1.6, 7.9 Hz), 7.76 (td, 1H, 4JH-F=1.6 Hz, J=1.6, 4.8 Hz); ESI-MS m/z 227.9 [M+H]+.