Hydrochloric Acid → HCID 178505495, compound

HRID 1935750Notes

Reaction equation

HRID 1935750 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([C:18]3[N:19]=[CH:20][N:21](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:22]=3)(O)[CH2:9]2)=[CH:4][CH:3]=1.Cl>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([C:18]3[N:19]=[CH:20][NH:21][CH:22]=3)=[CH:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22465357HCID 22465357, compound

Product 1

HCID 178505495HCID 178505495, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-(4-Fluorophenyl)-1-(1-trityl-1H-imidazol-4-yl)indan-1-ol (2.22 g) in 22 ml of a 2 M HCl solution was heated at 70° C. for 2 hr. Water was added. The mixture was extracted with methylene chloride. Then methylene chloride phase was extracted with 2 M HCl solution. All combined water layers were made basic and extracted with methylene chloride. The organic phase was washed with water and dried. The solvent was removed under reduced pressure. The crude 4-[3-(4-fluorophenyl)-3H-inden-1-yl]-1H-imidazole which was the mixture of isomers (the ratio 73:27) was purified by flash chromatography (elution with a dichloromethane-methanol gradient).

Workup

  1. extractionThe mixture was extracted with methylene chloride
  2. extractionThen methylene chloride phase was extracted with 2 M HCl solution
  3. extractionextracted with methylene chloride
  4. washThe organic phase was washed with water
  5. customdried
  6. customThe solvent was removed under reduced pressure
  7. additionthe mixture of isomers (the ratio 73:27)
  8. customwas purified by flash chromatography (
  9. washelution with a dichloromethane-methanol gradient)

Sources & evidence

ORD record
ord-563c99d0b1bf47a68ed9dbd56942ce8b
Source dataset
uspto-grants-2002_05
Patent number
US06388090B2

Reaction notes

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