Morpholine → HCID 67264195, compound

Participants

Reaction Steps

Morpholine (0.10 mL, 1.1 mmol) and 9-Ethyl-2-nitro-8,9-dihydro-5-oxa-9-aza-benzocyclohepten-7-one (74 mg, 0.31 mmol) in Methylene chloride (5 mL) was stirred for 4 h, then Sodium triacetoxyborohydride (0.13 g, 0.63 mmol) was added. After stirring overnight, a mixture of products was observed. The reaction mixture was partitioned between DCM and satd. sodium bicarbonate; the organic was washed with brine and dried over sodium sulfate. Chromatography (0-100% EtOAc:Hex) afforded 9-Ethyl-2-nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-ol (23 mg, 31%) and 9-Ethyl-7-morpholin-4-yl-2-nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene (60 mg, 60%). 1H-NMR (CDCl3): 7.55 (m, 2H), 6.88 (m, 1H), 4.45 (m, 1H), 4.34 (m, 1H), 3.72 (m, 5H), 3.37 (m, 3H), 3.01 (m, 1H), 2.66 (m, 4H), 1.25 (t, 3H, J=7.0 Hz).

Provenance & Evidence