Hydrochloric Acid → (+-)-Norketamine

HRID 2222567Notes

Reaction equation

HRID 2222567 reaction equation
[ClH:1].Cl.Cl[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]=CC1(O)CCCC1.[CH:18]1[CH:23]=[CH:22][C:21](C2C=CC=CC=2)=[CH:20][CH:19]=1.C1C=CC([O:36]C2C=CC=CC=2)=CC=1>>[CH:19]1[CH:20]=[CH:21][C:22]([Cl:1])=[C:23]([C:5]2([NH2:10])[C:4](=[O:36])[CH2:9][CH2:8][CH2:7][CH2:6]2)[CH:18]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 17856383HCID 17856383, compound

Product 1

HCID 123767(+-)-NorketamineYield 80%

Conditions

Temperature
200 °C

Procedure

To 250 ml of Dowtherm-A™ at 200° C. was added in one portion the hydrochloride of compound 3 (20 g, 0.077 mol) and the mixture was stirred at 200° C. for 15 minutes. The reaction mixture was then cooled at 110° C., and the precipitate formed was removed and discarded by filtration. The filtrate was diluted in ether and extracted in water (2×200 ml). The combined aqueous phases were washed with ether, made alkaline with 6N sodium hydroxide and extracted in ether (2×150 ml). The combined ether layers were washed with water, dried and concentrated to dryness. The residue obtained was purified by flash chromatography on silica gel (70% hexane/30% ethylacetate) to give norketamine free base (13.75 g, 80%) 4 as a colourless oil.

Workup

  1. temperatureThe reaction mixture was then cooled at 110° C.
  2. customthe precipitate formed
  3. customwas removed
  4. filtrationdiscarded by filtration
  5. additionThe filtrate was diluted in ether
  6. extractionextracted in water (2×200 ml)
  7. washThe combined aqueous phases were washed with ether
  8. extractionextracted in ether (2×150 ml)
  9. washThe combined ether layers were washed with water
  10. customdried
  11. concentrationconcentrated to dryness
  12. customThe residue obtained
  13. customwas purified by flash chromatography on silica gel (70% hexane/30% ethylacetate)

Sources & evidence

ORD record
ord-1b76e3988e374673bd913b58a2ee505c
Source dataset
uspto-grants-2008_05
Patent number
US07371829B2

Reaction notes

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