Aluminum(III) Chloride → N1,N1-Diethyl-1-(naphthalen-1-yl)-1,2-ethanediamine

HRID 2073719Notes

Reaction equation

HRID 2073719 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[N:11]([CH2:14][CH:15]([C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1)[N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[N+]=[N-]>C(OCC)C>[CH2:19]([N:16]([CH2:17][CH3:18])[CH:15]([C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1)[CH2:14][NH2:11])[CH3:20]

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 15057234HCID 15057234, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15057235N1,N1-Diethyl-1-(naphthalen-1-yl)-1,2-ethanediamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of 0.76 g (0.02 mol) of lithium aluminum hydride in 100 mL of dry diethyl ether under a nitrogen atmosphere and cooled to -10° to 0° C. add carefully in portions 10.67 g (0.08 mol) of aluminum chloride. When the initial reaction has ceased add dropwise a solution of 2.68 g (0.01 mol) of α-azidomethyl-N,N-diethyl-1-naphthalenemethanamine in 50 mL of diethylether. When the addition is complete allow the reaction mixture to warm to room temperature. Follow the progress of the reaction by thin-layer chromatography on silica gel. At the completion of the reaction carefully quench the excess reducing agent by the addition of sodium sulfate decahydrate. Filter the solids and wash the solids with 500 mL of hot methylene chloride. Dry the filtrate over anhydrous sodium sulfate. Filter the drying agent and remove the solvent in vacuo to obtain the title compound.

Workup

  1. temperaturecooled to -10° to 0° C.
  2. customWhen the initial reaction
  3. additionWhen the addition
  4. customthe progress of the reaction by thin-layer chromatography on silica gel
  5. customAt the completion of the reaction
  6. customcarefully quench the
  7. additionby the addition of sodium sulfate decahydrate
  8. filtrationFilter the solids
  9. washwash the solids with 500 mL of hot methylene chloride
  10. dry with materialDry the filtrate over anhydrous sodium sulfate
  11. filtrationFilter the drying agent
  12. customremove the solvent in vacuo

Sources & evidence

ORD record
ord-af102f9ac6e54a8aa897099f06ec6af3
Source dataset
uspto-grants-1990_04
Patent number
US04920116

Reaction notes

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