2,2'-(octylimino)bisethanol

Synthesis

The general procedure for the synthesis of 2,2'-(octylazadiyldiyl)diethanol from 1-bromooctane and diethanolamine was as follows: 1-bromooctane (3.0 g, 15.0 mmol), diethanolamine (2.4 g, 22.8 mmol), and anhydrous potassium carbonate (4.28 g, 31.0 mmol) were dissolved in acetonitrile (40 mL), and reacted for 12 h under nitrogen protection at reflux. After completion of the reaction, it was cooled to room temperature and the reaction mixture was concentrated. The organic phase was extracted with dichloromethane and dried with anhydrous sodium sulfate. The crude product was obtained after removing sodium sulfate by filtration under reduced pressure. The crude product was purified by column chromatography using dichloromethane and methanol as eluents to afford pure 2,2'-(octylazadiyldiyl)diethanol as a colorless oil (590 mg, 91% yield).1H NMR (CDCl3) data were as follows: δ 4.22 (brs, 2H, -OHCH2), 3.86 (t, 4H, J = 5 Hz, -CH2OH), 3.10 (t, 4H, J = 4.5 Hz, -CH2N), 2.94 (t, 2H, J = 8 Hz, -CH2N), 1.69-1.60 (m, 2H, -CH2), 1.30-1.25 (m, 10H, -CH2), 0.87 (t, 3H, J = 7 Hz, -CH3).

References

[1] Patent: WO2018/42367, 2018, A2. Location in patent: Page/Page column 95; 96-97
[2] Molecular Crystals and Liquid Crystals (1969-1991), 1990, vol. 185, p. 131 - 140
[3] Patent: CN106187790, 2016, A. Location in patent: Paragraph 0044-0050
[4] Patent: US2541088, 1946,
[5] European Journal of Medicinal Chemistry, 1976, vol. 11, p. 115 - 124