2-(Dimethylamino)ethanol → [2-(3-Isopropoxy-4-nitrophenoxy)ethyl]dimethylamine

Temperature

80 °C

N,N-Dimethylethanolamine (1.6 g, 18 mmol) was added to a mixture of powdered KOH (1.0 g, 18 mmol) and Aliquat 336 (0.72 g, 1.8 mmol), and the resulting mixture was stirred for 5 minutes at 80° C. Then 4-fluoro-2-isopropoxy-1-nitrobenzene (3.0 g, 15 mmol) was added, and stirring proceeded at this temperature for 30 minutes. The mixture was cooled and partitioned between methylene chloride (100 mL) and dilute aqueous HCl (100 mL), and the organic layer was extracted with dilute aqueous HCl (2×100 mL). The combined aqueous phases were washed with methylene chloride (3×150 mL), basified (3N NaOH), and extracted with methylene chloride (3×100 mL). The combined organic extracts were washed with water (3×100 mL), dried (MgSO4), and evaporated, providing 2.2 g as a yellow oil, in 55% yield; 1H NMR (CDCl3) δ 1.40 (d, J=6.1 Hz, 6H), 2.34 (s, 6H), 2.74 (t, J=5.6 Hz, 2H), 4.10 (t, J=5.6 Hz, 2H), 4.61 (septet, J=6.1 Hz, 1H), 6.48 (dd, J=9.1 Hz, J=2.5 Hz, 1H), 6.57 (d, J=2.5 Hz, 1H), 7.91 (d, J=9.1 Hz, 1H).

1. stirringstirring
2. waitproceeded at this temperature for 30 minutes
3. temperatureThe mixture was cooled
4. custompartitioned between methylene chloride (100 mL) and dilute aqueous HCl (100 mL)
5. extractionthe organic layer was extracted with dilute aqueous HCl (2×100 mL)
6. washThe combined aqueous phases were washed with methylene chloride (3×150 mL)
7. extractionextracted with methylene chloride (3×100 mL)
8. washThe combined organic extracts were washed with water (3×100 mL)
9. dry with materialdried (MgSO4)
10. customevaporated
11. customproviding 2.2 g as a yellow oil

ORD record

ord-06fa1a3835784defa51901fbd9cb2bc5

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08481568B2