Sodium Chloride → [4-(Tetradecyloxy)phenyl]methyl-2-pyridinecarboxamide

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Reaction Steps

To a room temperature suspension of 6.72 g of product from Example 114 in 200 ml methylene chloride is added, dropwise over 15 minutes, 10.05 g of product from Example 99 dissolved in 160 ml of methylene chloride. The reaction is stirred at room temperature for 10 minutes, followed by the dropwise addition of 12.73 g of triethylamine. The solution is stirred at room temperature for 19 hours, poured into a solution consisting of equal volumes saturated sodium bicarbonate, saturated sodium chloride and water, and extracted with 50/50 chloroform/methylene chloride. The organic layers are washed with saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel: 25% ethyl acetate/hexane) to give 10.75 g of the desired product as pale yellow crystals.

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