Morpholine → 4-[(4-Iodophenyl)carbonyl]morpholine

Participants

Reaction Conditions

Reaction Steps

1-(3-Dimethylaminopropyl)-3-ethylcarbodimide hydrochloride (12.1 g, 62.9 mmol), 1-hydroxybenzotriazole hydrate (9.63 g, 62.9 mmol), and morpholine (9.13 g, 105 mmol) was added to a solution of 4-iodobenzoic acid (13 g, 52.4 mmol) in a mixture of THF (250 mL) and methylene chloride (50 mL). After stirred at 25° C. for 20 hr, the solvent was removed and flash silica gel chromatography (step gradient elution with methylene chloride containing 0 to 3% MeOH) afforded (4-iodophenyl)(morpholino)-methanone (15.1 g). MS (ESI) m/z 317.9 (M+H). 1H NMR (CDCl3) δ ppm 7.76 (2H, d, J=8.24 Hz), 7.14 (2H, d, J=8.24 Hz), 3.23-4.00 (8H, m).

Provenance & Evidence