Triethylamine → HCID 69003367, compound

Participants

Reaction Steps

To a solution of 4-(4-Phenoxy-phenoxy)-piperidine (152 mg, 0.5 mmol) in anhydrous CH2Cl2 (0.5 mL) was added methyl-3-bromopropionate (91 mg, 0.55 mmol) in CH2Cl2 (0.5 mL) and triethylamine (101 mg, 1.0 mmol). The resulting mixture was purged with nitrogen and stirred at rt for 48 h. CH2Cl2 was removed in vacuo and crude mixture was partioned between EtOAc and water. EtOAc layer was removed, washed with saturated NaHCO3, dried over anhydrous MgSO4 and concentrated. The crude mixture was purified by silica gel flash chromatography (50% EtOAc/Hexane) to obtain the product (146 mg, 82%): MS; m/z 356.5 (M+H); 1H NMR (400 MHz, DMSO-d6); δ 1.56-1.60 (m, 2H), 1.89-1.92 (m, 2H), 2.19-2.49 (m, 2H), 2.46-2.49 (m, 2H), 2.58 (t, 2H, J=6.8Hz), 2.60-2.69 (m, 2H), 3.59 (s, 3H), 4.28-4.30 (m, 1H), 6.91-6.96 (m, 6H), 7.04-7.08 (m, 1H), 7.32-7.36 (m, 2H); HPLC (UV); 94.7%.

Provenance & Evidence