Allylamine → HCID 20225322, compound

HRID 1249189Notes

Reaction equation

HRID 1249189 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].Cl.Cl[CH2:7][CH2:8][N:9]([CH2:12][CH3:13])[CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+]>C(O)C.[OH-].[Na+]>[CH2:1]([NH:4][CH:8]([N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[CH3:7])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 7853AllylamineHCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochloride

Product 1

HCID 20225322HCID 20225322, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 49.7 g (0.87 moles) of allylamine in 500 ml of ethanol, add in several portions 50 g (0.29 moles) of 2-chloro-N,N-diethylethanamine hydrochloride, then add 80.2 g (0.58 moles) of potassium carbonate. Stir the reaction at room temperature for 1 hr, then heat to reflux. Follow the progress of the reaction by thin-layer chromatography on silica gel (acetonitrile:ammonium hydroxide, 9:1). At the completion of the reaction dilute the mixture with 500 ml of 20% sodium hydroxide solution. Extract the aqueous mixture with 4×200 ml of diethyl ether. Dry the combined ether extracts over anhydrous sodium sulfate. Remove the drying agent by filtration and evaporate the solvent in vacuo. Distill the residue at reduced pressure and collect the fraction distilling at 81° C. (20 mm Hg) to obtain the title compound.

Workup

  1. customthe reaction at room temperature for 1 hr
  2. temperatureheat to reflux
  3. customthe progress of the reaction by thin-layer chromatography on silica gel (acetonitrile:ammonium hydroxide, 9:1)
  4. extractionExtract the aqueous mixture with 4×200 ml of diethyl ether
  5. dry with materialDry the combined ether
  6. customRemove the drying agent
  7. filtrationby filtration
  8. customevaporate the solvent in vacuo
  9. distillationDistill the residue at reduced pressure
  10. customcollect the fraction
  11. distillationdistilling at 81° C. (20 mm Hg)

Sources & evidence

ORD record
ord-93778f3a035946f1b2ef0e89c6d1f5a5
Source dataset
uspto-grants-1986_12
Patent number
US04629739

Reaction notes

Loading…