Sodium Hydroxide → n-benzyl-2-methylpropan-1-amine

HRID 579839Notes

Reaction equation

HRID 579839 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7](=[N:14][CH2:15][CH:16]([CH3:18])[CH3:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+]>CCOCC>[CH3:17][CH:16]([CH3:18])[CH2:15][NH:14][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 118050676852-57-9HCID 21226445Aluminium lithium hydride

Product 1

HCID 211729n-benzyl-2-methylpropan-1-amineYield 90.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of lithium aluminum hydride (23 g, 606 mmol) in ether (115 ml) was added an ethereal solution (115 ml) of N-benzylidene-2-methyl-1-propanamine (72.1 g, 447 mmol) over a period of 45 minutes. It was then refluxed for one hour. The reaction mixture was cooled in an ice bath and while stirring vigorously, aqueous sodium hydroxide (20%, 120 ml) was added dropwise. The ether solution was separated, dried over magnesium sulfate and concentrated to dryness yielding 66.1 g of the title compound.

Workup

  1. temperatureIt was then refluxed for one hour
  2. temperatureThe reaction mixture was cooled in an ice bath
  3. customThe ether solution was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-67f93610a6b642f4894926ad22ab25d9
Source dataset
uspto-grants-1988_06
Patent number
US04749792

Reaction notes

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