Aluminium lithium hydride → beta-Methylbenzenepropanamine

HRID 398041Notes

Reaction equation

HRID 398041 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-a0d512eb41eb460489bd15aa7d4f83af
Source dataset
uspto-grants-2003_08
Patent number
US06610698B2

Reaction notes

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