Sodium Hydroxide → HCID 20283055, compound

Participants

Reaction Steps

To a suspension of 1.4 g (21.1 mmol) of lithium aluminum hydride (57% in oil; washed 3 times with hexane) in 50 ml of dry THF, cooled at 0°, was added dropwise a solution of 1-{N-{3-[2-(4-Fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylaminoacetyl}-4-(4-fluorophenoxy)piperidine (liberated from 5.94 g (10.5 mmol) of the oxalate) in 50 ml of dry THF. The mixture was allowed to warm to room temperature and was then heated at reflux for 16 hours under nitrogen, allowed to cool to room temperature and subsequently cooled in an ice bath. To the mixture were added dropwise, slowly, 0.7 ml of water, 0.7 ml of 15% NaOH and 2 ml of water. The mixture was filtered and washed with 100 ml of THF. The solvent was evaporated from the filtrate to provide an oil. The oil was dissolved in ether, washed with water and saturated sodium chloride and dried over potassium carbonate. Filtration followed by evaporation of the solvent provided an oil. The yield of the dihydrochloride was 3.83 g (68%). Recrystallization from ethanol provided analytically pure material.

Provenance & Evidence