Potassium Carbonate → HCID 22011775, compound

Participants

Reaction Steps

2-[2-(2-Benzylaminoethoxy)ethoxy]ethanol 32 (4.786 g, 20 mmol) and 2-bromoethylphthalimide (5.59 mL, 22 mmol) were dissolved in absolute acetonitrile (100 mL). Potassium carbonate (6.91 g, 50 mmol) was added, and the suspension was heated at reflux with vigorous stirring under an argon atmosphere for 18 hours. The suspension was allowed to cool to room temperature, diluted with acetonitrile (100 mL) and filtered through a Celite™ pad. The acetonitrile was removed under reduced pressure and the residue was purified by flash chromatography using a 1:1 mixture of 40% acetone in hexanes and chloroform as the eluent. Fractions contained the desired product (Rf=0.35) were combined, solvent removed under reduced pressure, and the residue dried in vacuo to provide the title compound 33 (4.2 g, 51%). CIMS (MH+): 413. 1H-NMR (CDCl3): δ 7.82 (m, 2H, phthalimide), 7.70 (m, 2H, phthalimide), 7.21 (m, 5H, phenyl), 4.39 (s, 2H, CH2-Ph), 3.70-3.21 (m, 12 H, OCH2CH2O), 2.85 (q, 2H, J=6.1 Hz, phthalimido-ethylene), 2.79 (q, 2H, J=6.4 Hz, phthalimido-ethylene). 13C-NMR (CDCl3): δ 168.8, 139.8, 134.3, 132.8, 129.4, 128.7, 128.0, 127.6, 73.1, 71.0, 70.8, 62.3, 59.9, 53.7, 52.4, 48.2, 45.1.

Provenance & Evidence