2-Nitropropane → 1-(4-Fluorobenzyl)-4-(1-methyl-1-nitroethyl)piperidin-2-one

Participants

Reaction Steps

To a solution 1-(4-fluorobenzyl)-5,6-dihydropyridin-2(1H)-one (see Step 3 of Example 1) (0.75 g, 3.65 mmol) in 2-nitropropane (9.77 g, 109 mmol) was added DBU (0.56 g, 3.65 mmol). After stirring for 48 hours, the reaction mixture was concentrated under vacuum. The residual material was purified using silica gel column chromatography eluting with CH2Cl2. The appropriate fractions were combined and concentrated to afford the title compound. 1H NMR (400 MHz, CDCl3) δ 7.44 (m, 2H), 7.04 (t, J=9 Hz, 2H), 4.64 (d, J=15 Hz, 1H), 4.43 (d, J=15 Hz, 1H), 3.23 (m, 2H), 2.56 (m, 2H), 2.22 (m, 1H), 1.73 (m, 1H), 1.56 (s, 6H), 1.51 (m, 1H) ppm. ES MS M+1=295.

Provenance & Evidence