Sodium Chloride → HCID 66711401, compound

Participants

Reaction Steps

In a 10-mL sealed tube was heated 4-(3-Iodoquinolin-8-yl)piperazine-1-carboxylic acid tert-butyl ester (520.0 mg, 1.184 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)-xanthene (137 mg, 0.2367 mmol), tris(dibenzylideneacetone)dipalladium(0) (108.4 mg, 0.1184 mmol), sodium tert-butoxide (341.3 mg, 3.551 mmol), and benzophenone imine (218 L, 1.30 mmol) in 13 mL toluene at 100° C. for 5 hours. The reaction was cooled and water and sodium chloride were added. The product was extracted with DCM, dried with sodium sulfate, filtered, and conc. in vacuo. Purification via silica gel chromatography eluting with 100:1 DCM:MeOH afforded the crude imine which was dissolved in 10 THF and treated with 10 drops of 12.1M aq. HCl at room temperature. Upon reaction completion, water and sat. NaHCO3 were added to the reaction whose contents were extracted with DCM. The combined extracts were dried with sodium sulfate, filtered, and conc. in vacuo. The crude material was purified via silica gel chromatography eluting with 50:1 DCM:MeOH to provide 4-(3-Aminoquinolin-8-yl)-piperazine-1-carboxylic acid tert-butyl ester as an off-white solid (182 mg, 44.5%). MP 168-173° C. LCMS (E/I+) 329.13 (M+H). 1H NMR (DMSO-d6)-8.37 (d, 1H, J=2.56 Hz), 7.23 (t, 1H, J=7.71 Hz), 7.18 (d, 1H, J=7.76 Hz), 7.08 (d, 1H, J=2.52 Hz), 6.74 (d, 1H, J=7.12 Hz), 5.58 (s, 2H), 3.59-3.51 (m, 4H), 3.25-3.19 (m, 4H), 1.43 (s, 9H).

Provenance & Evidence