Ammonium formate → ethyl 2-(propylamino)acetate

Temperature

80 °C

Ammonium formate (2 g, 31 mmol) was added to a solution of ethyl 2-[benzylpropylamino]acetate (1.05 g, 4.47 mmol) in ethanol (15 mL) and acetic acid (1 mL). The reaction vessel was then carefully flushed with nitrogen gas. Palladium on carbon (10%, 300 mg) was added in one portion, and the resulting mixture was heated at 80° C., under nitrogen for 3 h. The reaction mixture was allowed to cool to room temperature, and filtered through celite filteraid. The filtrate was concentrated in vacuo, (azeotroping with toluene (20 mL) to remove the acetic acid), to give ethyl 2-(propylamino)acetate as a yellow oil (quantitative crude yield). 1H NMR (CDCl3) δ 4.14 (q, J=7.1 Hz, 2H), 3.30 (s, 2H), 2.60 (dd, J=7.4 Hz, 2H), 1.50 (m, 2H), 1.26 (t, J=7.2 Hz, 3H), 0.89 (t, J=7.4 Hz, 3H).

1. customThe reaction vessel was then carefully flushed with nitrogen gas
2. additionPalladium on carbon (10%, 300 mg) was added in one portion
3. temperatureto cool to room temperature
4. filtrationfiltered through celite filteraid
5. concentrationThe filtrate was concentrated in vacuo
6. custom(azeotroping with toluene (20 mL)
7. customto remove the acetic acid),
8. customto give

ORD record

ord-fa6f7639f6ec418a92090d02045e091c

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07446204B2