4-Piperidinecarboxylic acid → 1-(4-fluorobenzoyl)piperidine-4-carboxylic acid

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Reaction Steps

Piperidine-4-carboxylic acid (25.8 g, 200 mmol) and potassium carbonate (82.9 g, 600 mmol) are combined in water (500 mL) and methylene chloride (1 L) at 0° C. 4-Fluorobenzoyl chloride (31.7 g, 200 mmol) is dissolved in methylene chloride (200 mL) and added to the first mixture dropwise over 45 min. The mixture is stirred for 2 hr, after which the aqueous layer is separated and acidified to pH 1.5 with concentrated HCl. The aqueous mixture is extracted three times with methylene chloride, and the organic extracts are dried over magnesium sulfate and evaporated to give the title compound.

Provenance & Evidence