Hydrochloric Acid → 7,7-Bis(3-Fluorophenyl)-4-perhydroisoindolone hydrochloride

HRID 1029933Notes

Reaction equation

HRID 1029933 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)[CH:16]3[CH:12]([CH2:13][N:14](C(OC=C)=O)[CH2:15]3)[C:11](=[O:22])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[ClH:30]>O1CCOCC1>[ClH:30].[F:29][C:25]1[CH:24]=[C:23]([C:8]2([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)[CH:16]3[CH:12]([CH2:13][NH:14][CH2:15]3)[C:11](=[O:22])[CH2:10][CH2:9]2)[CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67916103HCID 67916103, compound

Product 1

HCID 679158007,7-Bis(3-Fluorophenyl)-4-perhydroisoindolone hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

(3aRS,7aRS)-7,7-bis-(3-fluorophenyl)-2-vinyloxycarbonyl-4-perhydroisoindolone (64.5 g) is treated with a 6N solution (330 cc) of hydrochloric acid in dioxane for 30 minutes at 25° C. The solution is concentrated to dryness under reduced pressure (2.7 kPa) and the residue is taken up in ethanol (500 cc). The solution is heated at 60° C. for 6 hours and stirred for 16 hours at 25° C. and then concentrated to half its volume under reduced pressure (2.7 kPa) and the crystals formed are drained and washed with isopropyl ether and then dried. 7,7-Bis(3-Fluorophenyl)-4-perhydroisoindolone hydrochloride (48.7 g) is obtained. m.p.=264° C.

Workup

  1. concentrationThe solution is concentrated to dryness under reduced pressure (2.7 kPa)
  2. concentrationconcentrated to half its volume under reduced pressure (2.7 kPa)
  3. customthe crystals formed
  4. washwashed with isopropyl ether
  5. customdried

Sources & evidence

ORD record
ord-f6ef978905854ab89d11991531b4a5e1
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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