Sodium Hydroxide → HCID 53934672, compound

Participants

Reaction Conditions

Reaction Steps

To N-ethyl-4-(3-(1-methylethoxy)phenyl)-4-n-propylpiperidine (Preparation 65, 10.9 g) in toluene (80 ml) under nitrogen at 85° C. was slowly added phenyl chloroformate (5.63 ml, 44.88 mmol) over 20 min. The mixture was then heated under reflux for 4 h. The solution was cooled to 50° C. and 5M aqueous sodium hydroxide (10 ml) was added. Once the solution had cooled to room temperature the layers were separated and the organic extract was washed with methanol:1N aqueous hydrochloric acid (1:1, 2×10 ml), methanol 1N aqueous sodium hydroxide solution (1:1, 20 ml) and water (20 ml). The organic layer was dried (Na2SO4), filtered and concentrated in vacuo to give the crude product. This was purified by silica column chromatography using ethyl acetate:hexane:0.880 ammonia (15:85:1) to give the title compound as a pale yellow oil (6.9 g, 42% over three steps).

Provenance & Evidence