Water → 4-BUTOXYBENZYLAMINE

HRID 890802Notes

Reaction equation

HRID 890802 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) δ 7.16 (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-639e3e876f504943b161110cab35fe79
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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