Water → 2-ethylbenzenemethanamine

Temperature

0 °C

Lithium aluminum hydride (7.4 g 196 mmol) in tetrahydrofuran (130 mL) was slowly treated with 2-ethylbenzonitrile (4.99 g 38 mmol) in tetrahydrofuran (40 mL) at 0° C. under nitrogen. The mixture was stirred for 30 minutes at 0° C., 2 hours at room temperature, recooled to 0° C., and then slowly treated in succession with water (7.4 mL), 15% sodium hydroxide (7.4 mL) and water (22 mL). Additional tetrahydrofuran (50 mL) was added to facilitate stirring. The reaction mixture was filtered through celite, the filter cake was washed with tetrahydrofuran (150 mL), the filtrate was concentrated under reduced pressure, and the residue was partitioned between methylene chloride/saturated sodium chloride. The organic phase was dried (potassium carbonate), filtered, and the filtrate was concentrated under reduced pressure to provide the title compound. 1H NMR (CDCl3) δ 1.24 (t, 3H), 2.69 (q, 2H), 3.89 (s, 2H), 7.20 (m, 3H), 7.32 (m, 1H).

1. customrecooled to 0° C.
2. stirringto facilitate stirring
3. filtrationThe reaction mixture was filtered through celite
4. washthe filter cake was washed with tetrahydrofuran (150 mL)
5. concentrationthe filtrate was concentrated under reduced pressure
6. customthe residue was partitioned between methylene chloride/saturated sodium chloride
7. dry with materialThe organic phase was dried (potassium carbonate)
8. filtrationfiltered
9. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-9887e9dd56774134a460366033fd8f0c

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07709469B2