Ethanolamine → HCID 68380401, compound

Participants

Reaction Conditions

Reaction Steps

Synthesis of 2-({2-[(7-fluoronaphthalen-1-yl)oxy]ethyl}amino)ethanol (C41). A solution of 1-(2-chloroethoxy)-7-fluoronaphthalene (C40) (429 mg, 1.59 mmol) in N,N-dimethylformamide (8.9 mL) was treated with 2-aminoethanol (1.03 mL, 18.6 mmol) and heated to 80° C. for 18 hours. The reaction was cooled to room temperature, treated with saturated aqueous sodium bicarbonate solution (100 mL) and extracted with ethyl acetate (3×75 mL). The combined organic layers were washed with aqueous sodium hydroxide (1 M), dried over sodium sulfate and concentrated in vacuo. Purification via silica gel chromatography afforded the title compound as a colorless solid. Yield: 194 mg, 0.77 mmol, 48%. 1H NMR (400 MHz, CDCl3) δ 2.92-2.97 (m, 2H), 3.19 (dd, J=5.3, 5.1 Hz, 2H), 3.69-3.73 (m, 2H), 4.27 (dd, J=5.3, 5.1 Hz, 2H), 6.87 (d, J=7.6 Hz, 1H), 7.25-7.30 (m, 1H, assumed; partially obscured by solvent peak), 7.34 (dd, J=8.1, 7.7 Hz, 1H), 7.44 (d, J=8.2 Hz, 1H), 7.80 (dd, J=9.1, 5.6 Hz, 1H), 7.85 (dd, J=10.5, 2.5 Hz, 1H).

Provenance & Evidence