Sodium Hydroxide → 1,3-Dibenzylpiperidin-4-one

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Reaction Steps

1,3-Dibenzyl-4-oxo-piperidine-3-carboxylic acid methyl ester, (2, Y═H, Z=benzyl) (17.52 g, 51.92 mmol) was suspended in 150 mL of 6N HCl:MeOH (5:1) and the mixture was heated to reflux temperature with stirring for 48 h. After cooling the mixture was basified to pH 10 with 6N NaOH and extracted with 3×200 mL dichloromethane. The combined organics were dried (MgSO4) and concentrated to give 11.60 g of the title compound as a colorless oil, 80%. LC-MS: RT=0.38 min. (M+H)+ 280.

Provenance & Evidence