Beta-Nitrostyrene → Ethyl 3-[(2-amino-1-phenylethyl)amino]propanoate

Temperature

0 °C

Trans-□-Nitrostyrene (4.04 g, 27.1 mmol) was added to a solution of ethyl 3-aminopropanoate hydrochloride (4.16 g, 27.1 mmol), and N,N-diisopropylethylamine (9.43 mL, 54.2 mmol) in acetonitrile (70 mL). After 15 min, anhydrous hydrochloric acid gas was bubbled into the solution until acidic. The mixture was concentrated, redissolved in ethanol (60 mL) and aqueous hydrochloric acid (12 M; 30 mL), and cooled to 0° C. Zinc dust (8.80 g, 134 mmol) was added in portions over 5 min. After 0.5 h, the mixture was concentrated to remove ethanol and saturated aqueous sodium carbonate was added. The mixture was extracted with dichloromethane (3×), and the combined organic extracts were dried over magnesium sulfate, filtered and concentrated to give the title compound (9.5 g). MS 237 (M+1).

1. customanhydrous hydrochloric acid gas was bubbled into the solution until acidic
2. concentrationThe mixture was concentrated
3. dissolutionredissolved in ethanol (60 mL)
4. waitAfter 0.5 h
5. concentrationthe mixture was concentrated
6. customto remove ethanol and saturated aqueous sodium carbonate
7. additionwas added
8. extractionThe mixture was extracted with dichloromethane (3×)
9. dry with materialthe combined organic extracts were dried over magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated

ORD record

ord-1c98881dc1db454bb19725d22035e607

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07491713B2