7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one Chemical Properties

Boiling point:

504.5±50.0 °C(Predicted)

Density 

1.513

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

-1.23±0.20(Predicted)

Appearance

White to off-white Solid

7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one Usage And Synthesis

Synthesis

A mixed solution of 7,8-dimethoxy-3-(3-chloropropyl)-1,3-dihydro-2H-3-benzazepin-2-one (50.00 g, 169 mmol) with sodium iodide (32.75 g, 218 mmol) in methyl isobutyl ketone (375 mL) was reacted under argon protection at 117-118 °C with stirring. The reaction process was monitored by high performance liquid chromatography (HPLC). Upon completion of the reaction, the mixture was concentrated under reduced pressure and the residue was diluted with dichloromethane (375 mL) and water (190 mL). The organic phase was separated, washed with water (190 mL) and concentrated again under reduced pressure. The resulting residue was treated with methyl tert-butyl ether (190 mL) and the resulting suspension was cooled to 0 °C. After continuous stirring at 0 °C for 1 h, the solid product was collected by filtration, washed with methyl isobutyl ether (40 mL) and dried at 23 °C/100 mbar for 2 h. The final product was obtained as 60.10 g of light yellow solid product in 92% yield.

References

[1] Patent: WO2014/114341, 2014, A1. Location in patent: Page/Page column 15; 16
[2] Patent: WO2014/102827, 2014, A1. Location in patent: Paragraph 0121
[3] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 17, p. 2351 - 2354
[4] Patent: WO2010/72409, 2010, A1. Location in patent: Page/Page column 19-20
[5] Patent: WO2014/20534, 2014, A1. Location in patent: Page/Page column 13

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