Ethanol → Ethyl [1-acetyl-3-(4-methylbenzyl)piperidin-3-yl]acetate

Participants

Reaction Conditions

Reaction Steps

Silver nitrate (1.87 g, 11.0 mmol) was dissolved in 3 ml H2O. It was added to a solution of the product from STEP 6 (1.6 g, 5.5 mmol) in 25 ml ethanol. A solution prepared from dissolving NaOH (0.88 g, 22.0 mmol) in 4.0 ml H2O was added dropwise to the silver nitrate solution. The reaction was stirred at 25° C. for 2 h. The reaction was diluted with 15 ml H2O. The ethanol was removed and the resulting residue was extracted with ethyl acetate (2×60 ml). The aqueous extracts were acidified with 1 N aqueous HCl solution to PH=5, and extracted with ethyl acetate (3×100 ml). The organic layer was washed with 15 ml brine, dried with MgSO4, filtered and concentrated to afford a 1.1 g of clean oil. The oil was dissolved in 30 ml ethanol and 15 ml 2M HCl/dioxane. The reaction was stirred at room temperature for 18 h and concentrated. The residue was purified by chromatography (on silica gel, CH2Cl2/MeOH/NH4OH=95/5/0.1) to give 0.88 g of a gummy solid. The 1H NMR spectrum of the product was consistent for the proposed structure.

Provenance & Evidence