Triethylamine → HCID 67915770, compound

HRID 1029907Notes

Reaction equation

HRID 1029907 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:13][C:14]([OH:16])=O)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl.[C:18]1([C:24]2([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH:32]3[CH:28]([CH2:29][NH:30][CH2:31]3)[C:27](=[O:33])[CH2:26][CH2:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>ClCCl>[C:34]1([C:24]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:32]3[CH:28]([CH2:29][N:30]([C:14](=[O:16])[CH2:13][C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=4[N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)[CH2:31]3)[C:27](=[O:33])[CH2:26][CH2:25]2)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 212645437,7-Diphenylhexahydro-1H-isoindol-4(2H)-one hydrochlorideHCID 23009401HCID 23009401, compound

Product 1

HCID 67915770HCID 67915770, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N,N'-Carbonyldiimidazole (0.35 g) is added to a solution of 2-[2-(4-morpholinyl)phenyl]acetic acid (0.48 g) in dry dichloromethane (25 cc), cooled to +5° C. The mixture is stirred for 75 minutes at +5° C. and a solution of (3aRS,7aRS)-7,7-diphenyl-4-perhydroisoindolone hydrochloride (0.71 g) and triethylamine (0.6 cc) in dichloromethane (20 cc) is then added. The reaction mixture is stirred for 1 hour at +5° C. and then for 8 hours at 20° C. It is washed with distilled water (3×100 cc) and with saturated sodium chloride solution (100 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 (0.04-0.063 mm, diameter 2.2 cm, height 12 cm), eluting with a mixture of ethyl acetate and cyclohexane (70/30 by volume) under a nitrogen pressure of 0.7 bar and collecting 50 cc fractions. Fractions 4 and 5 are combined and concentrated to dryness under reduced pressure (2.7 kPa). The residue is recrystallized from ethylene oxide (2 cc). The crystals are drained, washed with isopropyl ether (1 cc) and dried. (3aRS,7aRS)-7,7-diphenyl-2-[2-[2-(4-morpholinyl)phenyl]acetyl]-4-perhydroisoindolone (0.27 g) melting at 167° C. is obtained.

Workup

  1. temperaturecooled to +5° C
  2. stirringThe reaction mixture is stirred for 1 hour at +5° C.
  3. waitfor 8 hours at 20° C
  4. washIt is washed with distilled water (3×100 cc) and with saturated sodium chloride solution (100 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 (0.04-0.063 mm, diameter 2.2 cm, height 12 cm)
  9. washeluting with a mixture of ethyl acetate and cyclohexane (70/30 by volume) under a nitrogen pressure of 0.7 bar
  10. customcollecting 50 cc fractions
  11. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  12. customThe residue is recrystallized from ethylene oxide (2 cc)
  13. washwashed with isopropyl ether (1 cc)
  14. customdried

Sources & evidence

ORD record
ord-d53c60d3892442e3bfd64027f5a72a00
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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