Water → 4-BUTOXYBENZYLAMINE

HRID 1699067Notes

Reaction equation

HRID 1699067 reaction equation
[CH2:1]([O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>CCOCC>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][NH2:11])=[CH:12][CH:13]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 138435p-ButoxybenzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 1436244-BUTOXYBENZYLAMINEYield 57%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 4-butoxybenzonitrile (4.6 g, 26.25 mmol) in Et2O (50 mL) was added lithium aluminum hydride (1.0 M in THF, 26.2 mL, 26.2 mmol) dropwise. The reaction was heated at reflux for 1 h and was cooled to room temperature. The reaction was carefully poured into water (50 mL) and was diluted with Et2O. The solids were removed by filtration through Celite with the aid of Et2O. The organic solution was washed with water followed by brine, dried (MgSO4), filtered, and concentrated in vacuo to provide 4-butoxybenzylamine (2.68 g). 1H NMR (400 MHz, CDCl3) δ7.16 (m, 2H), 6.82 (m, 2H), 3.91 (m, 2H), 3.75 (s, 2H), 1.73 (m, 2H), 1.46 (m, 2H), 1.39 (m, 2H), 0.95 (t, 3H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 1 h
  3. customThe solids were removed by filtration through Celite with the aid of Et2O
  4. washThe organic solution was washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3615c986c45d441786d12815d2a4939a
Source dataset
uspto-grants-2002_02
Patent number
US06344485B1

Reaction notes

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