Chloroacetyl chloride → 2-Chloro-1-[4-(4-methyl-3'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-6'-yl)-piperazin-1-yl]-ethanone

Participants

Reaction Conditions

Reaction Steps

A solution of 4-methyl-3′-nitro-6′-piperazin-1-yl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl dihydrobromide (as prepared in Example 67, step (c), 0.28 g, 0.60 mmol) in CH2Cl2 (6 mL) was treated with Et3N (0.27 mL, 1.9 mmol) and cooled to 0° C. The mixture was treated with chloroacetyl chloride (53 μL, 0.66 mmol) as a solution in CH2Cl2 (2 mL) and stirred at 0° C. for 15 min then at room temperature for 30 min. The reaction was diluted with CH2Cl2 and washed with water. The organic layer was dried over MgSO4 and concentrated in vacuo to afford the title compound (0.18 g, 80%) as a yellow solid. 1H-NMR (CDCl3; 400 MHz): δ 8.21 (d, 1H, J=9.2 Hz), 6.03 (d, 1H, J=9.2 Hz), 4.11 (s, 2H), 3.84-3.76 (m, 4H), 3.76-3.61 (m, 4H), 3.13-3.05 (m, 1H), 3.04-2.92 (m, 2H), 1.7-1.66 (m, 2H), 1.45-1.38 (m, 2H), 1.38-1.25 (m, 2H), 0.98 (d, 3H, J=6.4 Hz). LC-MS (ESI, m/z): Calcd. for C17H24ClN5O3, 382.1 (M+H), found 382.1.

Provenance & Evidence