2-Morpholinoethylamine → HCID 66893941, compound

Participants

Reaction Steps

7-Iodo-5-nitrobenzofuran (1.00 g, 3.46 mmol), 4-(2-aminoethyl)morpholine (0.54 g, 4.15 mmol), NaOt-Bu (0.47 g, 0.00484 mol), Xantphos (0.20 g, 0.346 mmol) and Pd2 dba3 (80 mg, 0.0865 mol) were heated in xylene (20 mL) at 120° C. for 1.5 hours. The reaction mixture was filtered through Celite and the solvent evaporated. The residue was run through a silica plug using dichloromethane (DCM) and then a 90:9:1 mixture of DCM/MeOH/NH3 (aqueous 25%) as eluents. The product-containing fractions were concentrated to yield 0.978 g (97%) of the title compound as a dark yellow oil. HPLC purity=97%, m/z=292 (M+H)+, 1H NMR (270 MHz, CDCl3) δ ppm 2.44-2.61 (m, 4H) 2.75 (t, J=5.81 Hz, 2H) 3.31-3.43 (m, 2H) 3.69-3.82 (m, 4H) 6.85 (d, J=1.98 Hz, 1H) 7.36 (d, J=1.98 Hz, 1H) 7.70 (d, J=1.98 Hz, 1H) 7.90 (d, J=2.23 Hz, 1H).

Provenance & Evidence