Triethylamine → HCID 67915959, compound

HRID 1029879Notes

Reaction equation

HRID 1029879 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.Cl.[C:13]1([C:19]2([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:27]3[CH:23]([CH2:24][NH:25][CH2:26]3)[C:22](=[O:28])[CH2:21][CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([N:25]2[CH2:24][CH:23]3[CH:27]([C:19]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH2:20][CH2:21][C:22]3=[O:28])[CH2:26]2)=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15880(4-Chlorophenyl)acetic acidHCID 212645437,7-Diphenylhexahydro-1H-isoindol-4(2H)-one hydrochloride

Product 1

HCID 67915959HCID 67915959, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N,N'-Carbonyldiimidazole (1.3 g) is added to a solution of 2-(4-chlorophenyl)acetic acid (1.36 g) in dry dichloromethane (30 cc), cooled to +5° C. The mixture is stirred for 1 hour at +5° C. and a solution of (3aRS,7aRS)-7,7-diphenyl-4-perhydroisoindolone hydrochloride (2.62 g) and triethylamine (1.12 cc) in dichloromethane (20 cc) is then added. The reaction mixture is stirred for 2 hours at +5° C. and 16 hours at 20° C.; it is washed with distilled water (3×50 cc), dried over magnesium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized from a mixture of acetonitrile (5 cc) and isopropyl ether (10 cc). The crystals obtained are drained and dried. The residue is recrystallized from acetonitrile (40 cc). The crystals obtained are drained, washed with isopropyl ether (10 cc) and dried. (3aRS,7aRS)-2-[(4-chlorophenyl)acetyl]-7,7-diphenyl-4-perhydroisoindolone (2.4 g) melting at 213° C. is obtained.

Workup

  1. temperaturecooled to +5° C
  2. stirringThe reaction mixture is stirred for 2 hours at +5° C. and 16 hours at 20° C.
  3. washit is washed with distilled water (3×50 cc)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe residue is crystallized from a mixture of acetonitrile (5 cc) and isopropyl ether (10 cc)
  8. customThe crystals obtained
  9. customdried
  10. customThe residue is recrystallized from acetonitrile (40 cc)
  11. customThe crystals obtained
  12. washwashed with isopropyl ether (10 cc)
  13. customdried

Sources & evidence

ORD record
ord-70f7df4714f841788de165ed6838572d
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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