Hydrochloric Acid → HCID 178419867, compound

HRID 279139Notes

Reaction equation

HRID 279139 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]23[CH2:17][CH2:16][CH:15](O)[CH:7]2[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=2[CH2:14]3)[N:3]=[CH:2]1.Cl.[H][H]>C(O)C.[Pd]>[CH2:17]1[C:6]2([C:4]3[N:3]=[CH:2][NH:1][CH:5]=3)[CH2:14][C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[CH:7]2[CH2:15][CH2:16]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 178418361HCID 178418361, compoundHCID 178515457HCID 178515457, compound

Product 1

HCID 178419867HCID 178419867, compoundYield 25.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 8a-(1H-imidazol-4-yl)-1,2,3,3a,8,8a-hexahydrocyclo-penta[a]inden-3-ol (0.5 g) in 20 ml of ethanol containing 5 ml of 20% hydrochloric acid was heated at reflux for 3 hours. The solution was allowed to cool to room temperature and 50 mg of 10% palladium on carbon catalyst was added. The reaction mixture was hydrogenated at 50-55° C. until no more hydrogen was consumed. The catalyst was filtered off and the solvent removed under reduced pressure. The residue was dissolved in water and the solution was basified with sodium hydroxide solution. The basic reaction solution was extracted with methylene chloride (3×100 ml), dried over sodium sulfate and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography using methylene chloride/methanol (97:3) as eluent. Recrystallization from ethyl acetate afforded 120 mg of product, m.p. 171-174° C.

Workup

  1. temperatureat reflux for 3 hours
  2. customwas consumed
  3. filtrationThe catalyst was filtered off
  4. customthe solvent removed under reduced pressure
  5. dissolutionThe residue was dissolved in water
  6. extractionThe basic reaction solution was extracted with methylene chloride (3×100 ml)
  7. dry with materialdried over sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customThe crude product was purified by flash chromatography
  10. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-ebbf362df95b4224841d75a1466e977c
Source dataset
uspto-grants-2002_03
Patent number
US06362211B1

Reaction notes

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