Water → N-Methyl-3-(benzyloxy)-benzeneethanamine

HRID 1271244Notes

Reaction equation

HRID 1271244 reaction equation
[H-].[Li+].[Al+3].[H-].[H-].[H-].[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH2:21][CH2:22][NH:23][CH:24]=O)[CH:18]=[CH:19][CH:20]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>O1CCCC1>[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH2:21][CH2:22][NH:23][CH3:24])[CH:18]=[CH:19][CH:20]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 229319731-[3-(Benzyloxy)phenyl]-2-(formylamino)ethane

Product 1

HCID 22931944N-Methyl-3-(benzyloxy)-benzeneethanamineYield 76.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.07 g of aluminum lithium hydride was suspended in 20 ml of tetrahydrofuran and a solution of 4.78 g of 1-[3-(benzyloxy)phenyl]-2-(formylamino)ethane in 10 ml of tetrahydrofuran was added dropwise at room temperature. The mixture was stirred at room temperature for 30 minutes and then heated at reflux for 2 hours. The reaction solution was ice-cooled and 1 ml of water, 1 ml of an aqueous 15% sodium hydroxide solution and 3 ml of water were added dropwise in order, followed by stirring for 30 minutes. The insoluble solid was removed by filtration and the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 3.46 g of the desired compound as a pale yellow oily substance.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. temperaturecooled
  4. stirringby stirring for 30 minutes
  5. customThe insoluble solid was removed by filtration
  6. customthe solvent in the filtrate was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ecf2e94bc1aa4d62bba534fd60397f3c
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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