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

HRID 1196241Notes

Reaction equation

HRID 1196241 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-vinyloxycarbonylperhydro-4-isoindolone (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 taken up with ethanol (500 cc). The solution is heated to 60° C. for 6 hours and stirred for 16 hours at 25° C., then concentrated to one half under reduced pressure (2.7 kPa), and the crystals formed are drained and washed with isopropyl ether, then dried. 7,7-Bis(3-fluorophenyl)perhydro-4-isoindolone 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 one half under reduced pressure (2.7 kPa)
  3. customthe crystals formed
  4. washwashed with isopropyl ether
  5. customdried

Sources & evidence

ORD record
ord-73dc76b3cdb84a54af2dc93b924c4251
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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