Phenethylamine → (2-Phenylethyl)propylamine

HRID 227279Notes

Reaction equation

HRID 227279 reaction equation
[C:1]1([CH2:7][CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:10](I)[CH2:11][CH3:12].C(N(CC)CC)C>O1CCCC1>[CH2:10]([NH:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 336431-Iodopropane

Product 1

HCID 3142088(2-Phenylethyl)propylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.2 ml (9.5 mmol) of phenylethylamine, 0.93 ml (9.5 mmol) of n-propyl-iodide, 5 ml of triethylamine and 5 ml of THF (tetrahydrofuran) were placed in a flask, and the reaction mixture was heated at reflux temperature of the reaction mixture for 3.5 hours and then cooled. A salt formed was filtered off, the solution was evaporated and a desired compound was purified by column chromatography on silica gel (silica gel 60, mobile phase: CHCl3:CH3OH=10:3). This yields 0.62 g (40%) of N-propyl-(β-phenylethyl)amine in the form of the oil (molecular weight: 163.264, formula: C11H17N).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux temperature of the reaction mixture for 3.5 hours
  3. temperaturecooled
  4. customA salt formed
  5. filtrationwas filtered off
  6. customthe solution was evaporated
  7. customa desired compound was purified by column chromatography on silica gel (silica gel 60, mobile phase: CHCl3:CH3OH=10:3)

Sources & evidence

ORD record
ord-782d417f33de43f2bb4ffa61161c59ce
Source dataset
uspto-grants-2009_07
Patent number
US07560474B2

Reaction notes

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