1-Hydroxybenzotriazole → HCID 44235961, compound

Participants

Reaction Steps

To a stirred solution of (4-phenylamino-benzoylamino)-acetic acid (0.087 g, 0.00032 mol) in DMF (5 mL) was added DIPEA (0.104 g, 0.00081 mol), HOBt (0.043 g, 0.00032 mol) and EDCI.HCl (0.061 g, 0.00032 mol) at ambient temperature. After 2 minutes 4-(2-bromo-phenoxy)-piperidine trifluoroacetate (0.1 g, 0.00027 mol) and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water and the product was extracted with ethyl acetate. The organic layer was washed with brine solution and dried over sodium sulfate. The organic layer was collected and concentrated under reduced pressure to afford 0.045 g (32%) of N-{2-[4-(2-bromo-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-4-phenylamino-benzamide. LCMS: 508.12 (M+1)+, 96.85%, 1H NMR (DMSO-d6): δ 8.6 (s, 1H), 8.3 (t, 1H), 7.8 (d, 2H), 7.6 (dd, 1H), 7.3 (m, 4H), 7.2 (d, 2H), 7.1 (d, 2H), 6.9 (q, 2H), 4.8 (m, 1H), 4.2 (t, 2H), 3.7 (m, 2H), 3.5 (m, 2H), 2.0 (m, 2H), 1.7 (m, 2H).

Provenance & Evidence