Potassium Carbonate → 2-(6-Chloropyridin-3-yl)-3-oxa-1-azaspiro[4.5]dec-1-ene

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Reaction Steps

To a solution of 6-chloro-N-[1-(hydroxymethyl)cyclohexyl]nicotinamide ax47 (2.17 g, 8.06 mmol, 1 eq) in chloroform (80 ml) is added thionyl chloride (1.8 ml, 24.18 mmol, 3 eq). The mixture is stirred at reflux for 2 h 30 before removing the volatiles under vacuum. The residue is dissolved in acetone and treated with potassium carbonate (2 eq), at reflux. After an aqueous work-up, the organic phase is dried over magnesium sulfate and concentrated in vacuo to give 1.86 g of a yellow solid. Purification over silicagel (eluent: dichloromethane/methanol/ammonia 99:1:0.1) finally yields 0.56 g of 2-(6-chloropyridin-3-yl)-3-oxa-1-azaspiro[4.5]dec-1-ene ax49.

Provenance & Evidence