Sodium Sulfate → beta-Methylbenzenepropanamine

HRID 566700Notes

Reaction equation

HRID 566700 reaction equation
[CH3:1][CH:2]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][NH-:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:1][CH:2]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][NH2:4]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 86587654HCID 86587654, compound

Product 1

HCID 12672558beta-Methylbenzenepropanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of commercially available 2-methyl-3-phenylpropylamide (4.32 g, 26.5 mmol) and lithium aluminium hydride (1.3 g, 34.3 mmol) in tetrahydrofuran (184 ml) was stirred at room temperature for 5 h. The reaction mixture was poured into saturated aqueous sodium sulfate and extracted with dichloromethane followed. The combined organic extracts were dried (sodium sulfate) and evaporated to provide the amine as an oil. For alternative preparations see: Dornow and Fust, Chem. Ber. 87, 984 (1954).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic extracts were dried (sodium sulfate)
  3. customevaporated

Sources & evidence

ORD record
ord-d09513c6392e44f0a85e5be2b943a22d
Source dataset
uspto-grants-2001_01
Patent number
US06174901B1

Reaction notes

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