Triethylamine → HCID 67915957, compound

HRID 1029905Notes

Reaction equation

HRID 1029905 reaction equation
Cl.[C:2]1([C:8]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:16]3[CH:12]([CH2:13][NH:14][CH2:15]3)[C:11](=[O:17])[CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[CH3:25]>ClCCl>[C:18]1([C:8]2([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:16]3[CH:12]([CH2:13][N:14]([C:11](=[O:17])[CH2:10][C:25]4[CH:4]=[CH:3][CH:2]=[CH:7][C:24]=4[N:26]4[CH2:29][CH2:30][CH2:28][CH2:27]4)[CH2:15]3)[C:11](=[O:17])[CH2:10][CH2:9]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

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

Product 1

HCID 67915957HCID 67915957, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N,N'-Carbonyldiimidazole (1.13 g) is added to a solution of 2-[2-(1-pyrrolydinyl)phenyl]acetic acid (1.42 g) in dry dichloromethane (30 cc), cooled to +5° C. The mixture is stirred for 40 minutes at +5° C. and a solution of (3aRS,7aRS)-7,7-diphenyl-4-perhydroisoindolone hydrochloride (2.3 g) and triethylamine (0.98 cc) in dichloromethane (20 cc) is then added. The reaction mixture is stirred for 1 hour at +5° C. and then for 1 hour at 20° C. It is washed with distilled water (2×20 cc), dried over magnesium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (0.2-0.063 mm, diameter 2 cm, height 25 cm), eluting with a mixture of ethyl acetate and cyclohexane (70/30 by volume) and collecting 100 cc fractions. Fractions 3 to 8 are combined and concentrated to dryness under reduced pressure (2.7 kPa). The residue is recrystallized from a mixture of acetonitrile (5 cc) and isopropyl ether (5 cc). The crystals are drained, washed with ethylene oxide (10 cc) and dried. (3aRS,7aRS)-7,7-diphenyl-2-[2-[2-(1-pyrrolidinyl)phenyl]acetyl]-4-perhydroisoindolone (2.2 g) melting at 178° C. is obtained.

Workup

  1. temperaturecooled to +5° C
  2. stirringThe reaction mixture is stirred for 1 hour at +5° C.
  3. waitfor 1 hour at 20° C
  4. washIt is washed with distilled water (2×20 cc)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)
  8. customThe residue is chromatographed on a silica gel column (0.2-0.063 mm, diameter 2 cm, height 25 cm)
  9. washeluting with a mixture of ethyl acetate and cyclohexane (70/30 by volume)
  10. customcollecting 100 cc fractions
  11. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  12. customThe residue is recrystallized from a mixture of acetonitrile (5 cc) and isopropyl ether (5 cc)
  13. washwashed with ethylene oxide (10 cc)
  14. customdried

Sources & evidence

ORD record
ord-8157aed121d94cff827f9a9132cd855d
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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