Benzoyl chloride → 4-Piperidineethanol, 1-benzoyl-

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Reaction Steps

Benzoyl chloride (25.8 ml) in dichloromethane (20 ml) was added dropwise over 30 minutes to a mixture of 4-(2-hydroxyethyl)piperidine (26 g) in dichloromethane (250 ml) and triethylamine (16.3 ml) at 0° C. The mixture was allowed to warm to ambient temperature and stirred at this temperature for 1 hour. The mixture was washed with sodium bicarbonate solution and then dried and evaporated to give a colourless oil. The oil was dissolved in 1,4-dioxane (250 ml) and then a solution of sodium hydroxide (5.0 g) in water (20 ml) was added and the mixture stirred at ambient temperature for 16 hours and then at 60° C. for 6 hours. The mixture was evaporated to near dryness, basified with 2M sodium hydroxide solution and the product extracted into dichloromethane to give 1-benzoyl-4-(2-hydroxyethyl)piperidine as an oil.

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