Propylamine → N-(2-Phenoxyethyl)propylamine

HRID 1730030Notes

Reaction equation

HRID 1730030 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].Br[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+]>>[O:8]([CH2:7][CH2:6][NH:4][CH2:1][CH2:2][CH3:3])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 7852PropylamineHCID 14798Sodium HydroxideHCID 68526Benzene, (2-bromoethoxy)-

Product 1

HCID 6453152N-(2-Phenoxyethyl)propylamine

Procedure

47.2 g. Propylamine was dissolved in 100 ml. absolute alcohol with cooling and 40.2 g. β-bromophenetole was added portionwise to the solution formed. After completion of the addition the reaction mixture was allowed to stand at room temperature for 1 week with occasional agitation. The excess of amine and solvent were then removed under vacuum from the steam bath and the residual colourless solid obtained on cooling was treated with an excess of 5N aqueous sodium hydroxide. An oil was liberated which was then extracted with ether, washed with water and dried over anhydrous sodium sulphate. After removal of the solvent the residual oil was distilled under vacuum to give N-2-phenoxyethyl-N-propylamine, boiling point 90°-92° C./0.2 mm.

Workup

  1. customformed
  2. additionAfter completion of the addition the reaction mixture
  3. waitto stand at room temperature for 1 week with occasional agitation
  4. customThe excess of amine and solvent were then removed under vacuum from the steam bath
  5. customthe residual colourless solid obtained
  6. temperatureon cooling
  7. extractionwas then extracted with ether
  8. washwashed with water
  9. dry with materialdried over anhydrous sodium sulphate
  10. customAfter removal of the solvent the residual oil
  11. distillationwas distilled under vacuum

Sources & evidence

ORD record
ord-01619e0dfa0141558b2d3bf9824625d9
Source dataset
uspto-grants-1976_11
Patent number
US03991071

Reaction notes

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