Ethanol → N-(2-Phenoxyethyl)propylamine

HRID 2371582Notes

Reaction equation

HRID 2371582 reaction equation
[O:1]([CH2:8][CH2:9]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:11]([NH2:14])[CH2:12][CH3:13].C(O)C>O>[CH2:11]([NH:14][CH2:9][CH2:8][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 702EthanolHCID 7852PropylamineHCID 12156Benzene, (2-chloroethoxy)-

Product 1

HCID 6453152N-(2-Phenoxyethyl)propylamineYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Into a 1-liter glass reactor, which can withstand a pressure of 6 atmospheres, fitted with a stirrer, heat-ing mantle and a pressure gauge, were added 100 g 2-phenoxy ethyl chloride, 150 g propyl amine, 130 ml ethanol and 100 ml water. The reaction was heated to 100° C. for 5 hours, during which time the pressure increased to 2.2 atmospheres. Afterwards the mixture was cooled to 50° C. to lower the pressure, the propyl amine was distilled off, about 200 ml of 20% aqueous HCl was added and the white hydrochloride precipitated out. This afforded 133 g having a purity of 95% in a yield of 93%.

Workup

  1. customInto a 1-liter glass reactor, which can withstand
  2. customa pressure of 6 atmospheres, fitted with a stirrer
  3. temperatureheat-ing mantle
  4. temperatureincreased to 2.2 atmospheres
  5. temperatureAfterwards the mixture was cooled to 50° C.
  6. distillationthe propyl amine was distilled off
  7. additionabout 200 ml of 20% aqueous HCl was added
  8. customthe white hydrochloride precipitated out

Sources & evidence

ORD record
ord-ba0dea2731894996a8ace18ef95a203e
Source dataset
uspto-grants-1992_03
Patent number
US05093526

Reaction notes

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