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

HRID 1196233Notes

Reaction equation

HRID 1196233 reaction equation
[C:1]1([C:7]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:15]3[CH:11]([CH2:12][N:13](C(OC=C)=O)[CH2:14]3)[C:10](=[O:21])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:28]>O1CCOCC1>[ClH:28].[C:22]1([C:7]2([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:15]3[CH:11]([CH2:12][NH:13][CH2:14]3)[C:10](=[O:21])[CH2:9][CH2:8]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67915936(3aRS,7aRS)-7,7-Diphenyl-2-vinyloxycarbonylperhydro-4-isoindolone

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

(3aRS,7aRS)-7,7-Diphenyl-2-vinyloxycarbonylperhydro-4-isoindolone (177 g) is treated with a 5.7N solution (1000 cc) of hydrochloric acid in dry dioxane for 30 minutes at 20° C. The solution is concentrated to dryness under reduced pressure (2.7 kPa) and the residue taken up in ethanol (500 cc), and the reaction mixture is stirred at 60° C. for 30 minutes and then cooled to +5° C. The crystals obtained are drained, washed with ethanol (50 cc) and dried. (3aRS,7aRS)-7,7-Diphenylperhydro-4-isoindolone hydrochloride (130 g), m.p. 270° C. with decomposition, is obtained.

Workup

  1. concentrationThe solution is concentrated to dryness under reduced pressure (2.7 kPa)
  2. temperaturecooled to +5° C
  3. customThe crystals obtained
  4. washwashed with ethanol (50 cc)
  5. customdried

Sources & evidence

ORD record
ord-132d174d635740d3aa6a706533ecc58f
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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