Potassium Iodide → 5-Chloro-2,3-dihydro-7-[3-[1-(3-methoxypropyl)-4-piperidinyl]-1,2,4-oxadiazol-5-yl]-4-benzofuranamine monohydrochloride

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl (3-chloropropyl) ether (1.6 g), intermediate 4 (3.9 g), triethylamine (5 ml) and potassium iodide (a catalytic amount) in dimethylformamide (60 ml) was stirred for 48 hours at 60° C. The reaction mixture was cooled and the solvent evaporated. The residue was partitioned between CH2Cl2 and a saturated aqueous NaCl solution. The organic layer was separated, dried over MgSO4, filtered and the solvent evaporated. The residue was purified by column chromatography on silica gel (eluent: CH2Cl2 /CH3OH 90/10). The desired fractions were collected and the solvent was evaporated. The residue was solidified in DIPE, filtered off, dissolved in 2-propanol and converted into the hydrochloric acid salt (1:1) with HCl/2-propanol. The precipitate was filtered off and dried, yielding 1.14 g (22.1%) of 5-chloro-2,3-dihydro-7-[3-[1-(3-methoxypropyl)-4-piperidinyl]-1,2,4-oxadiazol-5-yl]-4-benzofuranamine monohydrochloride.hemihydrate (compound 1; mp. 244.3° C.).

Provenance & Evidence