2-Bromoethanol → HCID 9860674, compound

HRID 1352424Notes

Reaction equation

HRID 1352424 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[NH:6][C:7]2=[O:12].C(=O)(O)[O-].[Na+].Br[CH2:25][CH2:26][OH:27]>C(#N)C>[OH:27][CH2:26][CH2:25][N:16]1[CH2:17][CH2:18][CH:13]([C:5]2[NH:6][C:7](=[O:12])[C:8]3[C:3]([CH:4]=2)=[C:2]([CH3:1])[CH:11]=[CH:10][CH:9]=3)[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 516892Sodium BicarbonateHCID 9965474HCID 9965474, compound

Product 1

HCID 9860674HCID 9860674, compoundYield 33.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Methyl-3-(piperidin-4-yl)-2H-isoquinolin-1-one (1.0 g), sodium bicarbonate (0.52 g) and 2-bromoethanol (0.67 g) were dissolved in acetonitrile (20 mL) and the solution was heated under reflux. After the completion of the reaction, the reaction mixture was concentrated and water was added to the obtained residue. The mixture was extracted with chloroform, and the extract was dried over magnesium sulfate. The solvent was concentrated and the obtained residue was purified by silica gel column chromatography to give 3-[1-(2-hydroxyethyl)piperidin-4-yl]-5-methyl-2H-isoquinolin-1-one (0.4 g).

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux
  3. customAfter the completion of the reaction
  4. concentrationthe reaction mixture was concentrated
  5. additionwater was added to the obtained residue
  6. extractionThe mixture was extracted with chloroform
  7. dry with materialthe extract was dried over magnesium sulfate
  8. concentrationThe solvent was concentrated
  9. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-91f6b392604e483a95e46f46e6df4993
Source dataset
uspto-grants-2007_05
Patent number
US07220759B2

Reaction notes

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