Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride → HCID 178517476, compound

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Reaction Steps

A mixture of 258 mg (11.2 mmol) of sodium in 10 mL of absolute ethanol was stirred at ambient temperature for 1 h. To the resultant sodium ethoxide solution was added 893 mg (3.0 mmol) of ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride in portions followed by 840 mg (3.72 mmol) of 6-(trifluoromethyl)pyridine-3-amidine hydrochloride. The reaction mixture was heated at reflux for 18 h, then concentrated in vacuo. To the residue was added ˜30 mL of 1N aqueous sodium hydroxide solution and 15 mL of water to give an insoluble solid and a yellow solution. The solid was filtered off and washed with water to provide 496 mg of the title compound. The aqueous filtrate was acidified to ˜pH 5 with concentrated hydrochloric acid and the solid precipitate was collected to give an additional 334 mg of the title compound as a bright yellow powder (72% total yield). LC-MS 387.2 (M+1).

Provenance & Evidence