5-Nonanone → HCID 178440921, compound

Participants

Reaction Steps

To a solution of (1R)-2-(1-benzothiophen-3-yl)-1-(4-phenyl-1H-imidazol-2-yl)-1-ethanamine (1 g, 2.5 mmol) in n-butanol (20 ml) was added 5-nonanone (2.2 ml, 13 mmol) and the mixture refluxed overnight. The solvent was removed under reduced pressure. To the residue was added water (15 ml) followed by a 10% NaHCO3 solution until neutral pH and extracted with ethyl acetate (3×20 ml). The combined organic extracts were washed with water (2×10 ml), dried over MgSO4, filtered. The solvent was evaporated under reduced pressure to afford an oil which was purified by column chromatography on silica gel using ethyl acetate/heptane 1:1 as eluent. After removing the solvent, diisopropyl ether was added to the residue. The resulting white precipitate was filtered off and washed with diisopropyl ether to afford 0.1 g of the title product. Melting point: 198-200° C.

Provenance & Evidence