Sodium Hydroxide → HCID 53987266, compound

Participants

Reaction Conditions

Reaction Steps

To N-ethyl-4-methyl-4-(3-(1-methylethoxy)phenyl)piperidine (Preparation 51, 3.98 g, 15.23 mmol) in toluene (30 ml) at 85° C. was slowly added phenyl chloroformate (2.1 ml, 16.75 mmol) and the mixture was then heated under reflux for 16 h. The solution was cooled to 45° C. and 50% w:v aqueous sodium hydroxide solution (2 ml) was added. Once the solution had cooled to room temperature the organic layer was separated and washed with methanol:1N aqueous hydrochloric acid (1:1, 3×10 ml), methanol:1N aqueous sodium hydroxide solution (1:1, 12 ml) and water (20 ml). The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give the crude product. This was purified by silica column chromatography using ethyl acetate:hexane (20:80) to give the title compound as an oil (2.5 g, 45% over three steps).

Provenance & Evidence