Oxalic Acid → HCID 86745163, compound

Participants

Reaction Steps

A mixture of 7.0 g (0.023 mole) of α,α-bis(4-fluorophenyl)-4-piperidinemethanol, 4.8 g (0.028 mole) of 5-chloro-N,N-dimethylpentanamide, 9.8 g (0.092 mole) of anhydrous sodium carbonate and 0.3 g (0.008 mole) of potassium iodide in 100 ml of N,N-dimethylformamide was heated on a steam bath for 16 h. The mixture was poured into 1.5 L of water and extracted twice with 200 ml portions of ethyl acetate. The ethyl acetate fractions were combined, washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to give a viscous oil. The oil was purified by column chromatography using 250 g of silica gel on a 69 cm×4 cm column, eluted with 10% methanol in methylene chloride. The fractions containing the desired product were combined and concentrated under reduced pressure to give a viscous oil. The oil was converted to the oxalic acid salt and the solid was recrystallized from 2-propanol to yield 6.2 g (52%) of white solid, mp 193°-195° C.

Provenance & Evidence