HCID 11153426, compound → HCID 19842259, compound

HRID 280542Notes

Reaction equation

HRID 280542 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-41d26b5abaa84b9fad190e62d0ef5866
Source dataset
uspto-grants-1986_05
Patent number
US04590189

Reaction notes

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