Potassium Iodide → Cis-4-amino-5-chloro-N-{1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl}-2-[2-(methylthio)ethoxy]benzamide monohydrate

Participants

Reaction Conditions

Reaction Steps

The product from Step A (0.45 g, 1 mmole) was added to a stirred suspension of sodium hydride (40 mg, 1 mmole of 60%, washed with petroleum ether) in acetonitrile (10 ml) followed by tetrabutylammonium bromide (0.32 g, 1 mmole). The reaction mixture was heated to 40° C. for 15 minutes, and there was then added 2-chloro-ethyl methyl sulfide (0.44 g, 4 mmole) and potassium iodide (50 mg). The mixture was heated to reflux for 2 hours. The solvent was evaporated and the residue was partitioned between ethyl acetate (containing 10% of methylene chloride) and water. The organic layer was dried and the solvent evaporated to leave a residue. The residue was crystallized from 2-propanol to yield 0.26 g (50%) of the title compound, mp. 58°-60° C.

Provenance & Evidence