N,N'-Dimethylethylenediamine → 10-(4-Trifluoromethyl-phenyl)-1,4-dioxa-10-aza-dispiro[4.2.4.2]tetradecan-9-one

Participants

Reaction Conditions

Reaction Steps

1,4-Dioxa-10-aza-dispiro[4.2.4.2]tetradecan-9-one (4 g) was dissolved in DMF (189 ml) at RT under an argon atmosphere. Then, 1-bromo-4-(trifluoromethyl)benzene (6.39 g), N,N′-dimethylethylenediamine (sym) (3.34 g), cuprous iodide (5.41 g) and K3PO4 (7.13 g) were added and the mixture was heated at 100° C. for 12 hours. The reaction mixture was cooled to RT, filtered and saturated aqueous NH4Cl solution was added. The mixture was then extracted twice with AcOEt, the combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated off in vacuo. The crude product was purified by flash chromatography (silica gel, gradient of 0% to 25% of acetronitrile in CH2Cl2) to give the title compound as white crystalline solid (4 g). MS (m/e): 356.146 [MH+].

Provenance & Evidence