Benzylethanolamine → Ethyl (4-benzylmorpholin-2-yl)acetate

Temperature

25 °C

2-(Benzylamino)ethanol (19.05 ml, 132 mmol) and triethylamine (18.44 ml, 132 mmol) was added to water (150 ml) and the resulting mixture was heated to reflux temperature. (E)-Ethyl 4-bromobut-2-enoate (18.24 ml, 132 mmol) was added dropwise for 10 min The resulting mixture was further maintained at reflux temperature for 5 h. The reaction mixture was cooled to 25° C. and added NaOH (5.29 g, 132 mmol) after that the solvent was removed by distillation under reduced pressure to give orange oil. Ethyl acetate (150 mL) was added and the resulting solution was washed with water (2×50 mL). Ethyl acetate was distilled off under reduced pressure to give crude compound (15 g). This crude compound was purified by flash chromatography (Biotage) using eluent 20% ethyl acetate in hexane to yield 13 g of pure title compound as colorless viscous oil. m/z 264.08.

1. temperaturethe resulting mixture was heated
2. temperatureto reflux temperature
3. temperaturewas further maintained
4. temperatureat reflux temperature for 5 h
5. customwas removed by distillation under reduced pressure
6. customto give orange oil
7. washthe resulting solution was washed with water (2×50 mL)
8. distillationEthyl acetate was distilled off under reduced pressure
9. customto give crude compound (15 g)
10. customThis crude compound was purified by flash chromatography (Biotage)

ORD record

ord-a78af227dd354035adb7a0f759ac4a99

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382216B2