Sodium Sulfate → HCID 563266, compound

HRID 850458Notes

Reaction equation

HRID 850458 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][C:22]#[N:23])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][CH2:22][NH2:23])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 5612222-BenzyloxyphenylacetonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 563266HCID 563266, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

LAH (1.04 g, 0.0273 mol, 3.0 eq) was dissolved in THF (25 ml), and to this solution was added dropwise a THF solution (25 ml) of (2-benzyloxyphenyl)-acetonitrile (2.04 g, 0.0091 mol, 1.0 eq) under ice-cooling. After the completion of the dropwise addition, the mixture was stirred at room temperature for 15 minutes and refluxed under heating for 2 hours. This reaction mixture was cooled with ice-cold water, and a saturated aqueous sodium sulfate solution (about 30-40 ml) was added. After filtration through Celite, the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (chloroforn/methanol=5/1) to give 2-(2-benzyloxyphenyl)ethylamine (0.415 g, 20.0%) as a pale-yellow amorphous compound.

Workup

  1. temperaturecooling
  2. additionAfter the completion of the dropwise addition
  3. temperaturerefluxed
  4. temperatureunder heating for 2 hours
  5. temperatureThis reaction mixture was cooled with ice-cold water
  6. filtrationAfter filtration through Celite
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained residue was purified by column chromatography (chloroforn/methanol=5/1)

Sources & evidence

ORD record
ord-c56bc94ff2694cb0891615538ed13200
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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