Sodium Sulfate → 4-(Benzyloxy)-benzenepropanamine

HRID 850461Notes

Reaction equation

HRID 850461 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]#[N:24])=[CH:17][CH:16]=1)[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:16]=[CH:17][C:18]([CH2:21][CH2:22][CH2:23][NH2:24])=[CH:19][CH:20]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 103541463-(4-Benzyloxyphenyl)propionitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 193633624-(Benzyloxy)-benzenepropanamineYield 49.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

LAH (570 mg, 0.015 mol, 1.5 eq) was dissolved in THF (30 ml), and to this solution was added dropwise a THF solution (50 ml) of 3-(4-benzyloxyphenyl)-propionitrile (2.37 g, 0.01 mol, 1.0 eq) under ice-cooling. After the completion of the dropwise addition, the mixture was stirred at room temperature 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 (chloroform/metanol=10/1-5/1) to give 3-(4-benzyloxyphenyl)propylamine (1.2 g, 49.7%) as a pale-yellow amorphous compound.

Workup

  1. temperaturecooling
  2. additionAfter the completion of the dropwise addition
  3. temperatureThis reaction mixture was cooled with ice-cold water
  4. filtrationAfter filtration through Celite
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by column chromatography (chloroform/metanol=10/1-5/1)

Sources & evidence

ORD record
ord-a2169fba1383420ba8c9c6fbd0ae8675
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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