Nitrogen → 5-(Morpholin-4-yl)-2,3-dihydro-1H-inden-1-one

Participants

Reaction Steps

A mixture of 5-bromo-1-indanone (0.76 g, 3.60 mmol), Cs2CO3 (1.64 g, 5.04 mmol), Pd2(dba)3 (82 mg, 0.09 mmol), BINAP (112 mg, 0.18 mmol), morpholine (0.94 mL, 10.8 mmol) and THF (15 ml) was pumped with N2 for 0.5 hour and then heated to reflux overnight. The reaction mixture was concentrated, and purified by flash chromatography to give the above intermediate (0.40 g, 51.1%). MS (ESI) m/z 218 (M+H)+; 1H NMR (300 MHz, CD3OD) δ ppm 2.59-2.65 (m, 2H) 3.03-3.10 (m, 2H) 3.34-3.40 (m, 4H) 3.79-3.85 (m, 4H) 6.95 (s, 1H) 6.99 (m, 1H) 7.57 (d, J=8.48 Hz, 1H).

Provenance & Evidence