Tributyltin Chloride → HCID 51002308, compound

Participants

Reaction Conditions

Reaction Steps

2-[4-(2,6-Dichloro-benzyloxy)-phenyl]-4-[2-(2H-tetrazol-5-yl)-ethyl]-morpholine hydrochloride: To a solution of 3-{2-[4-(2,6-dichloro-benzyloxy)-phenyl]-morpholin-4-yl}-propionitrile (0.30 g; 0.77 mmol) in xylene (10 mL) was added tributyltin chloride (0.46 mL; 1.7 mmol) and NaN3 (110 mg; 1.7 mmol). The resulting mixture was heated at 120° C. for two days. After cooling to RT the mixture was treated with methanol (10 mL) and concentrated in vacuo. The residue was purified by column chromatography (EtOAc:methanol 90:10 to 50:50) to afford 2-[4-(2,6-dichloro-benzyloxy)-phenyl]-4-[2-(2H-tetrazol-5-yl)-ethyl]-morpholine as the free base (0.30 g), The free base was treated with a solution of HCl in 1,4-dioxane, after stirring at RT for 4 hours, the salt precipitated. The salt was collected by filtration, washed with Et2O and dried in vacuo to afford 2-[4-(2,6-dichloro-benzyloxy)-phenyl]-4-[2-(2H-tetrazol-5-yl)-ethyl]-morpholine hydrochloride (0.30 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.15-3.29 (m, 2H) 3.53-3.75 (m, 6H) 4.06-4.22 (m, 2H) 4.94 (d, J=11.0 Hz, 1H) 5.24 (s, 2H) 7.11 (d, J=8.6 Hz, 2H) 7.36 (d, J=8.6 Hz, 2H) 7.45-7.52 (m, 1H) 7.58 (d, J=8.3 Hz, 2H) 12.31 (bs, 1H).

Provenance & Evidence