Triethylamine → HCID 67915986, compound

HRID 1029881Notes

Reaction equation

HRID 1029881 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=O.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>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([N:25]1[CH2:24][CH:23]2[CH:27]([C:19]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:20][CH2:21][C:22]2=[O:28])[CH2:26]1)=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 877542-Bromophenylacetic acidHCID 212645437,7-Diphenylhexahydro-1H-isoindol-4(2H)-one hydrochloride

Product 1

HCID 67915986HCID 67915986, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N,N'-Carbonyldimidazole (1.13 g) is added to a solution of 2-(2-bromophenyl)acetic acid (1.5 g) in dry dichloromethane (30 cc), cooled to +5° C. The mixture is stirred for 45 minutes at +5° C. and a solution of (3aRS,7aRS)-7,7-diphenyl-4-perhydroiso-indolone hydrochloride (2.3 g) and triethylamine (0.98 cc) in dichloromethane (40 cc) is then added. The reaction mixture is stirred for 4 hours at 20° C. The reaction mixture 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 recrystallized from acetonitrile (74 cc). The crystals are drained, washed with isopropyl ether (10 cc) and dried. (3aRS,7aRS)-2-[(2-bromophenyl)acetyl]-7,7-diphenyl-4-perhydroisoindolone (2.04 g) melting at 217° C. is obtained.

Workup

  1. temperaturecooled to +5° C
  2. stirringThe reaction mixture is stirred for 4 hours at 20° C
  3. washThe reaction mixture 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 recrystallized from acetonitrile (74 cc)
  8. washwashed with isopropyl ether (10 cc)
  9. customdried

Sources & evidence

ORD record
ord-ae7db6f7788c4401a0103e44f3f3a891
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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