HCID 519044, compound → HCID 19842221, compound

HRID 280538Notes

Reaction equation

HRID 280538 reaction equation
[CH:1]1([N:7]2[CH:15]([OH:16])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]2=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:18]1([C:24]([CH:26]=P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C1(C)C=CC=CC=1>[CH:1]1([N:7]2[CH:8]([CH2:26][C:24]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:25])[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:15]2=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 519044HCID 519044, compoundHCID 11153426HCID 11153426, compound

Product 1

HCID 19842221HCID 19842221, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1.2 g of 2-cyclohexyl-3-hydroxyisoindolin-1-one and 2.2 g of piperidinocarbonylmethylenetriphenylphosphorane in toluene (30 ml) was refluxed for 3 hours. After cooling, the toluene was distilled off and ether was added whereupon triphenylphosphine oxide separated out. After filtration, the filtrate was allowed to stand to giving crude crystals. Recrystallization from ether gave 1.3 g of 2-cyclohexyl-3-piperidinocarbonylmethylisoindolin-1-one.

Workup

  1. temperatureAfter cooling
  2. distillationthe toluene was distilled off
  3. additionether was added whereupon triphenylphosphine oxide
  4. customseparated out
  5. filtrationAfter filtration
  6. customto giving crude crystals
  7. customRecrystallization from ether

Sources & evidence

ORD record
ord-8d15becc6a6f4edfaab33069c76ba171
Source dataset
uspto-grants-1986_05
Patent number
US04590189

Reaction notes

Loading…