Triethylamine → N-[2-[N-ethyl-N-(2-hydroxyethyl)amino]ethyl]phthalimide

Reaction equation

[CH2:1]([NH:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16])[CH3:2].Br[CH2:18][CH2:19][OH:20].C(N(CC)CC)C>C(O)C>[CH2:1]([N:3]([CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16])[CH2:18][CH2:19][OH:20])[CH3:2]

Participants

Procedure

To a solution of compound 2 (15.00 g, 68.7 mmol) in anhydrous ethanol (300 mL) were successively added, under argon, 2-bromoethanol (14.8 mL, 0.21 mol) and triethylamine (29.0 mL, 0.21 mol). The mixture was stirred under reflux for 60 h. After cooling to room temperature, the solvent was evaporated under vacuum and the residue was chromatographed (SiO2, AcOEt/EtOH, 99/1, v/v) to give compound 3 (13.00 g, 49.6 mmol) as a white solid. Yield 72%; Rf (SiO2, AcOEt/EtOH, 99/1, v/v) 0.49; mp 56-58° C.; IR (KBr) ν 1018, 1387, 1405, 1702, 2825, 2959, 3400-3600 cm−1; 1H NMR (200 MHz, CDCl3) δ 0.93 (t, 3H, J=7.1 Hz), 2.58 (q, 2H, J=7.1 Hz), 2.68 (t, 2H, J=5.3 Hz), 2.76 (t, 2H, J=6.2 Hz), 3.11 (se, 1H), 3.53 (t, 2H, J=5.3 Hz), 3.77 (t, 2H, J=6.2 Hz), 7.71 (m, 2H), 7.82 (m, 2H); MS m/z 262 (M+, 1), 231 (11), 174 (21), 130 (8), 102 (100), 76 (10), 58 (29).