Hydrochloric Acid → HCID 89315326, compound

HRID 1518902Notes

Reaction equation

HRID 1518902 reaction equation
[NH2:1][O:2][CH3:3].Cl.CC(O[Na])=O.[CH3:10][NH:11][C:12]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=2[Cl:25])[C:17](=O)[CH2:16][CH2:15][CH2:14][CH2:13]1>CO.O.O>[CH3:3][O:2][N:1]=[C:13]1[CH2:14][CH2:15][CH2:16][CH2:17][C:12]1([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=1[Cl:25])[NH:11][CH3:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3821KetamineHCID 4113O-MethylhydroxylamineHCID 178418247HCID 178418247, compound

Product 1

HCID 89315326HCID 89315326, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

To as solution of NH2OMe. HCl and CH3COONa. H2O in MeOH:H2O (7:3) stirred at room temperature for 15 minutes, was added ketamine and the resulting solution was stirred at reflux for 16 hrs before cooling to room temperature. The reaction mixture was filtered and the filtrate was partitioned between CH2Cl2 and sat. NaHCO3 solution. The filtrate was extracted with CH2Cl2 (2×30 mL) and the combined organic layer was washed with brine solution. The organic layer was dried over anhydrous. Na2SO4 and concentrated under reduced pressure. The crude reaction mixture received was purified over silica gel column chromatography by eluting with initially CH2Cl2 and later with (1:9) MeOH:CH2Cl2 to receive methoxime 3 as pale yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.9-8.0 (m, 1H), 7.2-7.4 (m, 3H), 3.91-4.0 (m, 3H), 3.3 (td, J=4.10, 13.96 Hz, 1H), 3.2 (td, J=4.49, 13.73 Hz, 1H), 2.4-2.5 (m, 3H), 2.1-2.3 (m, 1H), 1.6-1.8 (m, 3H), 1.4-1.5 (m, 1H), 1.2-1.4 (m, 1H). 13C NMR (101 MHz, CDCl3) δ 156.3, 135.5, 132.4, 132.2, 131.9, 131.0, 128.3, 67.4, 62.7, 39.4, 28.8, 26.1, 24.7, 22.0.

Workup

  1. temperatureat reflux for 16 hrs
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was partitioned between CH2Cl2 and sat. NaHCO3 solution
  4. extractionThe filtrate was extracted with CH2Cl2 (2×30 mL)
  5. washthe combined organic layer was washed with brine solution
  6. customThe organic layer was dried over anhydrous
  7. concentrationNa2SO4 and concentrated under reduced pressure
  8. customThe crude reaction mixture
  9. customreceived was purified over silica gel column chromatography
  10. washby eluting with initially CH2Cl2 and later with (1:9) MeOH

Sources & evidence

ORD record
ord-0e2765653b874ee9b893d4315eaccd1a
Source dataset
uspto-grants-2015_07
Patent number
US09073819B2

Reaction notes

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