Morpholine → HCID 59441669, compound

Participants

Reaction Steps

To a solution of 5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole (0.5 g, 2.57 mmols) and polymer-bound diisopropyl ethylamine (2.10 g, 7.73 mmol) in dichloromethane (50 mL) was added bromoacetyl chloride (0.49 g, 3.11 mmol) via a dropwise addition. After stirring for 2 hrs at room temperature the solids were removed by vacuum filtration. The filtrate was concentrated under reduced pressure, maintained under high vacuum for several hours, redissolved in THF (20 mL) and to this crude mixture was added potassium carbonate (1.06 g, 7.68 mmols), catalytic Kl, and morpholine (0.67 g, 7.68 mmols). After overnight stirring, the reaction was diluted with dichloromethane (50 mL), washed with water (25 mL), filtered through a cotton plug and concentrated by rotary evaporation to provide 5-(methyloxy)-1-(4-morpholinylacetyl)-6-nitro-2,3-dihydro-1H-indole (0.56 g, 67% over two steps). ESIMS (M+H)+=322.

Provenance & Evidence