Triethylamine → Nalbuphine propionate

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Reaction Steps

75 mL of methylene chloride and 3.75 g (0.01 mole) of nalbuphine were added to a 250-mL round-bottomed flask. The flask was placed in an ice bath to keep it cool. The content was then stirred and then gradually a 20 mL of methylene chloride solution containing 0.16 mole of triethylamine was added. With rapid stirring, another 20 mL of methylene chloride solution containing 0.011 mole of dry propionic anhydride was added drop by drop. Afterward, the mixture was stirred at room temperature for 1 hour. 20 mL of 10% sodium carbonate solution was added to neutralize the residual acid and remove the water soluble impurities. Sodium sulfate was used to dehydrate the solution. After drying under vacuum, a nalbuphine propionate solid was obtained. The product was purified by column chromatography. The physical data are shown in Table 1 and FIGS. 4 and 5.

Provenance & Evidence