Ethyl Acetate → N1-Methyl-N1-phenylbutane-1,4-diamine

HRID 2225900Notes

Reaction equation

HRID 2225900 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([CH2:9][CH2:10][CH2:11][N:12]([CH3:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)#[N:8].C(OCC)(=O)C>CCOCC>[NH2:8][CH2:7][CH2:9][CH2:10][CH2:11][N:12]([CH3:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 19438634HCID 19438634, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19438630N1-Methyl-N1-phenylbutane-1,4-diamineYield 106.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Lithium aluminium hydride (2 g) was added to dry ether (50 ml) in a stream of nitrogen, and a solution of N-(3-cyanopropyl)-N-methylaniline (9 g) in dry ether (10 ml) was added dropwise. The mixture was stirred for 1 hour and then heated under reflux for 2 hours. After decomposition of the excess reducing agent with ethyl acetate, the organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated to obtain the desired compound (9.8 g) as colorless oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. washthe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a96ab9ed150b494fa0e69add80f6308e
Source dataset
uspto-grants-1994_09
Patent number
US05344928

Reaction notes

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