1,2-Dichloroethane → (4-Isopropyl-piperazin-1-yl)-(5-piperidin-1-ylmethylpyrazin-2-yl)-methanone

Participants

Reaction Steps

A mixture of 5-piperidin-1-ylmethyl-pyrazine-2-carboxylic acid (0.125 g, 0.53 mmol),1-isopropyl-piperazine dihydrochloride (0.117 g, 0.58 mmol), HOBt (0.086 g, 0.64 mmol) and N-methylmorpholine (0.323 g, 3.19 mmol) in DCM (7 mL) was stirred for 1 h. The mixture was then treated with EDC (0.122 g, 0.64 mmol) and stirring was continued for 18 h. The reaction was quenched by the addition of 1 N NaOH (10 mL), and was stirred for 30 min. The mixture was diluted with H2O (10 mL) and extracted with DCM (3×15 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated to yield the crude product (0.145 g). The crude was purified on SiO2 using 0-5% 2 M NH3 in MeOH/DCM to provide the title compound (0.05 g, 26%). MS (ESI): exact mass calcd. for C18H29N5O, 331.46; m/z found 332.5 [M+H]+. 1HNMR (500 MHz, CDCl3): 8.85 (d, J=1.4,1H), 8.64 (d, J=1.4, 1H), 3.82 (t, J=4.9, 2H), 3.68 (s, 2H), 3.63 (t, J=4.9, 2H), 2.77-2.70 (m, 1H), 2.62 (t, J=4.9, 2H), 2.53 (t, J=4.9, 2H), 2.48-2.42 (m, 4H), 1.63-1.57 (m, 4H), 1.49-1.42 (m, 2H), 1.05 (d, J=6.6, 6H).

Provenance & Evidence