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

HRID 1029869

Reaktionsgleichung

Reaktionsgleichung von HRID 1029869
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]>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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

(3aRS,7aRS)-2-benzyl-7,7-diphenyl-4-perhydroisoindolone (150 g), methanol (1,500 cc) and 1N hydrochloric acid (450 cc) are added to 10% palladiumon-charcoal (15 g); the reaction mixture is hydrogenated, with stirring, at ambient temperature and under atmospheric pressure. After a reaction time of 5 hours, the theoretical volume of hydrogen has been absorbed; the reaction mixture is filtered and the filtrate is then concentrated to dryness under reduced pressure (2.7 kPa); the residue is crystallized from ethanol (200 cc); the crystals obtained are drained, washed with ethanol (50 cc) and dried. (3aRS,7aRS)-7,7-diphenyl-4-perhydroisoindolone hydrochloride (110 g) melting at 270° C. with decomposition is obtained.

Aufarbeitung

  1. customAfter a reaction time of 5 hours, the theoretical volume of hydrogen has been absorbed
  2. filtrationthe reaction mixture is filtered
  3. concentrationthe filtrate is then concentrated to dryness under reduced pressure (2.7 kPa)
  4. customthe residue is crystallized from ethanol (200 cc)
  5. customthe crystals obtained
  6. washwashed with ethanol (50 cc)
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-60cce762045f4227a0d3baf4cd14267c
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05102667

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