Formamide, N-(2-phenylethyl)- → N-Methylbenzeneethanamine

HRID 1405518Notes

Reaction equation

HRID 1405518 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([NH:15][CH:16]=O)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O1CCCC1>[CH3:16][NH:15][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 140995Formamide, N-(2-phenylethyl)-HCID 21226445Aluminium lithium hydride

Product 1

HCID 11503N-Methylbenzeneethanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Into a 250-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of LiAlH4 (868 mg, 22.84 mmol, 1.50 equiv) in tetrahydrofuran (70 mL). This was followed by the addition of a solution of N-phenethylformamide (2.27 g, 15.23 mmol, 1.00 equiv) in tetrahydrofuran (50 mL) dropwise with stirring while the resulting solution maintained reflux. The resulting solution was stirred overnight at reflux in an oil bath. The reaction was then quenched by the addition of water. The resulting solution was extracted with 4×30 mL of dichloromethane and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (100:1). This resulted in 1.36 g (34%) of N-methyl-2-phenylethanamine as yellow oil.

Workup

  1. customInto a 250-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperaturemaintained
  4. temperaturereflux
  5. stirringThe resulting solution was stirred overnight
  6. temperatureat reflux in an oil bath
  7. customThe reaction was then quenched by the addition of water
  8. extractionThe resulting solution was extracted with 4×30 mL of dichloromethane
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under vacuum
  11. customThis resulted in 1.36 g (34%) of N-methyl-2-phenylethanamine as yellow oil

Sources & evidence

ORD record
ord-a8cff3e19fb44174a8f149ad584c9cb2
Source dataset
uspto-grants-2014_12
Patent number
US08916560B2

Reaction notes

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