Potassium Carbonate → HCID 59410241, compound

Participants

Reaction Conditions

Reaction Steps

To 2-(3-bromo-propoxy)-6-methyl-phenylamine (4.8 g, 20 mmol) in acetonitrile (200 mL) was added potassium carbonate (13.8 g, 100 mmol). The mixture was heated at 70° C. for 24 hrs, followed by the filtration to remove solids. After evaporation, the mixture was repartitioned with ethyl acetate (250 mL) and water (150 mL). The organic layer was then washed with brine (150 mL) and dried over MgSO4. Evaporation followed by purification by silica gel column chromatography eluting with hexane/ethyl acetate (11/1 to 4/1) yielded 1-methyl-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene 2-3 as a pale yellow oil (2.25 g). MS: 164.0 (M+H)+; tR=1.191 min (method 1). NMR (CDCl3), δ, 6.789-6.858 (2H, m), 6.664 (1H, t), 4.158 (2H, t), 3.343 (2H, t), 2.198 (3H, s), 1.191-2.067 (2H, m).

Provenance & Evidence