Diisopropylethylamine → HCID 22181339, compound

Participants

Reaction Steps

A mixture of N,N-diethyl-4-fluoro-3-nitrobenzamide (0.500 g, 2.08 mmol), N1,N1-dimethyl-1,2-propanediamine (0.636 g, 6.24 mmol), DIPEA (2.2 mL, 12.5 mmol) and DMF (12 mL) was stirred 4 hours at room temperature. The reaction was then concentrated in vacuo, the residue was dissolved in 2 N NaOH (30 mL) and extracted with CH2Cl2 (3×40 mL). The combined organic phases were washed with brine (10 mL) dried over MgSO4, filtered, and concentrated in vacuo. The crude reaction mixture was purified by silica gel column chromatography (100% CH2Cl2 to 5% MeOH/CH2Cl2) to provide the title compound (0.621 g, 93%) as a bright yellow solid. 1H-NMR (CDCl3): δ 8.33 (d, J=6.4 Hz, 1H), 8.27 (d, J=2.0 Hz, 1H), 7.55 (dd, J=8.8 Hz, J=2.0 Hz, 1H), 6.91 (d, J=9.6 Hz, 1H), 3.79 (heptet, J=7.2 Hz, 1H), 3.45 (br d, J=5.2 Hz, 4H), 2.55 (dd, J=12.0 Hz, J=7.6 Hz, 1H), 2.39 (dd, J=12.4 Hz, J=5.8 Hz, 1H), 2.29 (s, 6H), 1.69 (br s, 1H), 1.31 (d, J=6.8 Hz, 2H), 1.22 (t, J=7.4 Hz, 6H). MS (ESI) (M+H)+=323.

Provenance & Evidence