Ethanolamine → 2-[(4-Methoxybenzyl)amino]ethanol

Temperature

0 °C

A 1 L round bottom flask is charged with 2-aminoethanol (29 g, 213 mmol), 4-methoxybenzaldehyde (39 g, 639 mmol), methanol (250 mL) and acetic acid (75 mL) under a nitrogen atmosphere. The contents were cooled to 0° C. and sodium triacetoxyborohydride (50 g, 234 mmol) was added over a 20 minute period. The reaction mixture was stirred at room temperature for 18 hours, concentrated under reduced pressure and partitioned between water (500 mL) and ethyl acetate (500 mL). The ethyl acetate layer was washed with 3N HCl (400 mL). The HCl layer is separated, cooled to 0° C., made basic using 6N NaOH and extracted with dichloromethane (2×100 mL). The dichloromethane layer was dried over sodium sulfate and concentrated under reduced pressure to yield the title compound a as an oil (20 g). 1H-NMR of the oil was consistent with the desired structure.

1. concentrationconcentrated under reduced pressure
2. custompartitioned between water (500 mL) and ethyl acetate (500 mL)
3. washThe ethyl acetate layer was washed with 3N HCl (400 mL)
4. customThe HCl layer is separated
5. temperaturecooled to 0° C.
6. extractionextracted with dichloromethane (2×100 mL)
7. dry with materialThe dichloromethane layer was dried over sodium sulfate
8. concentrationconcentrated under reduced pressure

ORD record

ord-7a31ab6623104d0e8851f93e9c4dfdd3

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07943617B2