Ketamine → Ketamine

HRID 2370093Notes

Reaction equation

HRID 2370093 reaction equation
[CH3:1][NH:2][C:3]1([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=2[Cl:16])[C:8](=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4]1.[C:17]([O-:20])([O-])=[O:18].[Na+].[Na+].ClC([O:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)=O>C1(C)C=CC=CC=1>[N+:33]([C:30]1[CH:31]=[CH:32][C:27]([O:26][NH:2][C:17](=[O:18])[O-:20])=[CH:28][CH:29]=1)([O-:35])=[O:34].[CH3:1][NH:2][C:3]1([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=2[Cl:16])[C:8](=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 3821KetamineHCID 10340Sodium CarbonateHCID 821294-Nitrophenyl chloroformate

Product 2

HCID 3821KetamineHCID 86653325HCID 86653325, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

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)+.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. customToluene was evaporated under vacuum
  4. additionthe reaction mixture was diluted with dichloromethane (DCM)
  5. washThe DCM layer was washed 6 times with 50% aqueous NaHCO3 solution
  6. customto remove the para-nitrophenol side-product
  7. dry with materialThe DCM layer was then dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c242577575db4139809e0cf831707ff6
Source dataset
uspto-grants-2014_04
Patent number
US08710070B2

Reaction notes

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