4-Methylmorpholine → HCID 86755933, compound

Participants

Reaction Conditions

Reaction Steps

4-(3-Bromo-8-chloro-5,11-dihydro[1]benzoxepino[4,3-b]pyridin-11-ylidene)-piperidine (270 mg, 0.68 mmol), 4-pyridine-acetic acid 1-oxide (260 mg, 1.69 mmol), HOBT (200 mg, 1.48 mmol), and EDCl (320 mg, 1.67 mmol) were mixed and stirred at 0° C. in DMF (10 ml, anhydrous). NMM (0.5 ml, 4.53 mmol) was added, and the reaction mixture was stirred 2 hours at 0° C. and then overnight at 20° C. The solvent was evaporated off, water (20 ml) was added, and the mixture was extracted with methylene chloride (3×50 ml) and the extract was dried (MgSO4), filtered and evaporated, yielding a crude product which was chromatographed on silica gel and eluted with 12%ethylacetate/hexanes containing 2% ammonium hydroxide. The product was recrystallized from ether to afford a white powder, 4-(3-bromo-8-chloro-5,11-dihydro[1]benz-oxepino[4,3-b]pyridin-11-ylidene)-1-(4-pyridine-acetyl)piperidine N1-oxide (260 mg, 72%); MS (FAB, M+H)=526.

Provenance & Evidence