Phenylacetyl chloride → HCID 86745796, compound

HRID 1196285Notes

Reaction equation

HRID 1196285 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[C:12]1([C:18]2(C3C=CC=CC=3)[CH:26]3[CH:22]([CH2:23][NH:24][CH2:25]3)[C:21](=[O:27])[CH:20]=[CH:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N([CH2:39][CH3:40])CC)C>ClCCl>[C:12]1([CH:18]2[C:26]3([C:40]4[CH:39]=[CH:3][CH:2]=[CH:1][CH:6]=4)[CH:22]([CH2:23][N:24]([C:8](=[O:9])[CH2:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH2:25]3)[C:21](=[O:27])[CH:20]=[CH:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 67916164136916-30-8

Product 1

HCID 86745796HCID 86745796, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phenylacetyl chloride (0.82 cc) is added to a solution, cooled to +5° C., of 7,7-diphenyl-2,3,3a,4,7,7a-hexahydro-1H-isoindol-4-one hydrochloride (2 g) and triethylamine (1.7 cc) in dry dichloromethane (20 cc). The reaction mixture is stirred for 1 hour at +5° C. and for 1 hour at room temperature; it is washed with distilled water (2×20 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized in acetonitrile (15 cc). The crystals are drained, washed with isopropyl ether (10 cc), dried and then recrystallized in acetonitrile (20 cc). The crystals obtained are drained and dried. (3aRS, 7aRS)-7,7a-Diphenyl-2-(phenylacetyl)-2,3,3a,4,7,7a-hexahydro-1H-isoindol-4-one (2.7 g), m.p. 188° C., is obtained.

Workup

  1. washit is washed with distilled water (2×20 cc)
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe residue is crystallized in acetonitrile (15 cc)
  6. washwashed with isopropyl ether (10 cc)
  7. customdried
  8. customrecrystallized in acetonitrile (20 cc)
  9. customThe crystals obtained
  10. customdried

Sources & evidence

ORD record
ord-b741b008992245e9a3ccabd98c897528
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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