Ammonia → HCID 67915871, compound

HRID 1196268Notes

Reaction equation

HRID 1196268 reaction equation
[NH3:1].F[B-](F)(F)F.C(O[C:10](=[N+:18]1[CH2:26][CH:25]2[CH:20]([C:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:22][CH2:23][C:24]2=[O:27])[CH2:19]1)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)C.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[NH:1]=[C:10]([N:18]1[CH2:26][CH:25]2[CH:20]([C:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:22][CH2:23][C:24]2=[O:27])[CH2:19]1)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 11430Potassium CarbonateHCID 86745792HCID 86745792, compound

Product 1

HCID 67915871HCID 67915871, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 0.8N solution (8.8 cc) of ammonia in dichloromethane is added to a stirred suspension, cooled to -20° C., of (3aRS,7aRS)-2-(1-ethoxy-2-phenylethylidene)-4-oxo-7,7-diphenylperhydroisoindolium tetrafluoroborate (3.75 g) in anhydrous dichloromethane (30 cc). The reaction mixture is allowed to return to room temperature and stirring is continued for 5 hours. The reaction mixture is treated with 10% strength aqueous potassium carbonate solution (30 cc). The precipitate present is removed by filtration and the organic phase is then washed with distilled water (15 cc) and with saturated aqueous sodium chloride solution (15 cc), dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is recrystallized in acetonitrile (22 cc). The crystals obtained are drained and dried. (3aRS,7aRS)-2-(α-Iminophenethyl)-7,7-diphenylperhydro-4-isoindolone (1.3 g), m.p. 202° C., is obtained.

Workup

  1. customto return to room temperature
  2. customThe precipitate present is removed by filtration
  3. washthe organic phase is then washed with distilled water (15 cc) and with saturated aqueous sodium chloride solution (15 cc)
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe residue is recrystallized in acetonitrile (22 cc)
  7. customThe crystals obtained
  8. customdried

Sources & evidence

ORD record
ord-d4bd3d48660b4def82bbc153cb5040db
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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