HCID 178419843, compound → HCID 178420067, compound

HRID 1935757Notes

Reaction equation

HRID 1935757 reaction equation
[C:1]1([CH:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16]3[N:17]=[CH:18][NH:19][CH:20]=3)=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(=O)C.[Pd]>[C:1]1([CH:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]([C:16]3[N:17]=[CH:18][NH:19][CH:20]=3)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 178419843HCID 178419843, compound

Product 1

HCID 178420067HCID 178420067, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

The mixture of the isomers of 4-(3-phenyl-3H-inden-1-yl)-1H-imidazole was hydrogenated in acetic acid at 50° C. using 10% palladium on charcoal as a catalyst. The mixture was filtered through Celite, and the solvent was evaporated. Water was added and the solution was made basic. The water solution was extracted with ethyl acetate. The organic phase was washed with water, dried and the solvent was evaporated. The hydrochloride salt of the product was made in ethyl acetate. The product 4-(2,3-dihydro-3-phenylinden-1-yl)-1H-imidazole was the mixture of the cis and trans diastereomers (the ratio 95:5).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe solvent was evaporated
  3. additionWater was added
  4. extractionThe water solution was extracted with ethyl acetate
  5. washThe organic phase was washed with water
  6. customdried
  7. customthe solvent was evaporated
  8. additionthe mixture of the cis and trans diastereomers (the ratio 95:5)

Sources & evidence

ORD record
ord-c916f9d383184889b1e65327c38b13bf
Source dataset
uspto-grants-2002_05
Patent number
US06388090B2

Reaction notes

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