Aluminium lithium hydride → beta-Methylbenzenepropanamine

HRID 480425Notes

Reaction equation

HRID 480425 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-]>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

4

Reactant 2

HCID 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. It was poured into aqu. sat. sodium sulfate and extracted with dichloromethane followed by drying of the organic solution and evaporation to provide the amine as an oil. Other syntheses have been reported, e.g. Dornow and Fust, Chem. Ber. 87, 984 (1954).

Workup

  1. additionIt was poured into aqu
  2. extractionsat. sodium sulfate and extracted with dichloromethane
  3. customby drying of the organic solution and evaporation

Sources & evidence

ORD record
ord-c973db2897cc4949969af62c0d33e442
Source dataset
uspto-grants-2003_11
Patent number
US06649604B2

Reaction notes

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