Ketamine → Ketamine

Participants

Reaction Conditions

Reaction Steps

To a mixture of ketamine (0.052 g, 0.22 mmol) in anhydrous toluene (2 mL) and Na2CO3 (0.082 g) was added a solution of para-nitrophenyl chloroformate (0.129 g, 0.64 mmol) in anhydrous toluene (2 mL). After heating for 8 hours at 100° C., the reaction mixture was cooled to room temperature and filtered. Toluene was evaporated under vacuum and the reaction mixture was diluted with dichloromethane (DCM). The DCM layer was washed 6 times with 50% aqueous NaHCO3 solution to remove the para-nitrophenol side-product and then with brine. The DCM layer was then dried over anhydrous sodium sulfate, filtered, concentrated under vacuum to afford the para-nitrophenoxycarbamate of ketamine as a pale solid. MS (ESI) m/z 403 (M+H)+.

Provenance & Evidence