Hydrochloric Acid → 7,7-Diphenylhexahydro-1H-isoindol-4(2H)-one hydrochloride

HRID 2399993Notes

Reaction equation

HRID 2399993 reaction equation
C([N:8]1[CH2:16][CH:15]2[CH:10]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:12][CH2:13][C:14]2=[O:17])[CH2:9]1)C1C=CC=CC=1.[ClH:30]>[Pd].CO>[ClH:30].[C:24]1([C:11]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:10]3[CH:15]([CH2:16][NH:8][CH2:9]3)[C:14](=[O:17])[CH2:13][CH2:12]2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 19384608(3aRS, 7aRS)-2-benzyl-7,7-diphenyl-4-perhydroisoindolone

Product 1

HCID 212645437,7-Diphenylhexahydro-1H-isoindol-4(2H)-one hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

150 g of (3aRS,7aRS)-2-benzyl-7,7-diphenyl-4-perhydroisoindolone, 1500 cm3 of methanol and 450 cm3 of 1N hydrochloric acid are added to 15 g of 10% palladium on charcoal; the reaction mixture is hydrogenated, with stirring, at room temperature and at atmospheric pressure. The theoretical volume of hydrogen was absorbed after 5 hours of reaction; the reaction mixture is filtered and then concentrated to dryness under reduced pressure (2.7 kPa); the residue is crystallized from 200 cm3 of ethanol; the crystals obtained are drained, washed with 50 cm3 of ethanol and dried. 110 g of (3aRS,7aRS)-7,7-diphenyl-4-perhydroisoindolone hydrochloride are obtained; melting point 270° C., with decomposition.

Workup

  1. customThe theoretical volume of hydrogen was absorbed after 5 hours of reaction
  2. filtrationthe reaction mixture is filtered
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customthe residue is crystallized from 200 cm3 of ethanol
  5. customthe crystals obtained
  6. washwashed with 50 cm3 of ethanol
  7. customdried

Sources & evidence

ORD record
ord-3129d6577bec4badb5e5c14f88482aa0
Source dataset
uspto-grants-1995_09
Patent number
US05451601

Reaction notes

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