HCID 11153426, compound → HCID 19842259, compound

HRID 1638342Notes

Reaction equation

HRID 1638342 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:17]([OH:18])[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[C:10]2=O)=[CH:5][CH:4]=1.[N:20]1([C:26]([CH:28]=P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH:10]([CH2:28][C:26]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:27])[C:11]3[CH2:12][CH2:13][CH2:14][CH2:15][C:16]=3[C:17]2=[O:18])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 11153426HCID 11153426, compoundHCID 12234949HCID 12234949, compound

Product 1

HCID 19842259HCID 19842259, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(4-Methoxyphenyl)-3-hydroxy-4,5,6,7-tetrahydroisoindolin-1-one (2.59 g) and piperidinocarbonylmethylenetriphenylphosphorane (4.6 g) were dissolved in 50 ml of dry toluene and the solution was refluxed gently for 20 hours. After cooling, the solvent was distilled off and the residue was purified by silica gel column chromatography. Fractions eluted with dichloromethaneethyl acetate (5:1) were collected and concentrated to give crude crystals. This product was recrystallized from ether-hexane (1:3) to give 1.87 g of 2-(4-methoxyphenyl)-3-piperidinocarbonylmethyl-4,5,6,7-tetrahydroisoindolin-1-one.

Workup

  1. temperaturethe solution was refluxed gently for 20 hours
  2. temperatureAfter cooling
  3. distillationthe solvent was distilled off
  4. customthe residue was purified by silica gel column chromatography
  5. washFractions eluted with dichloromethaneethyl acetate (5:1)
  6. customwere collected
  7. concentrationconcentrated
  8. customto give crude crystals
  9. customThis product was recrystallized from ether-hexane (1:3)

Sources & evidence

ORD record
ord-7989a0ac6a9d4e2caf9ca7c75790fb62
Source dataset
uspto-grants-1989_11
Patent number
US04879293

Reaction notes

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