N-Benzyl-N,N'-dimethylethylenediamine → HCID 178484273, compound

HRID 1788912Notes

Reaction equation

HRID 1788912 reaction equation
[O:1]1[CH:11]2[CH:2]1[C:3](=[O:13])[C:4]1[C:9]([C:10]2=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:14]([N:21]([CH3:26])[CH2:22][CH2:23][NH:24][CH3:25])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[OH:1][C:11]1[C:10](=[O:12])[C:9]2[C:4]([C:3](=[O:13])[C:2]=1[N:24]([CH3:25])[CH2:23][CH2:22][N:21]([CH3:26])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

4

Reactant 2

HCID 66016N-Benzyl-N,N'-dimethylethylenediamineHCID 858442,3-Epoxy-2,3-dihydro-1,4-naphthoquinone

Product 1

HCID 178484273HCID 178484273, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.61 g of 2,3-epoxy-2,3-dihydro-1,4-naphthoquinone, 2.67 g of N-benzyl-N,N'-dimethylethylenediamine and 150 ml of absolute ethanol was stirred for 20 hours, then concentrated to one-half its original volume and refrigerated overnight. The solvent was removed, the residue dissolved in dichloromethane and passed through a pad of hydrous magnesium silicate and silica, eluting first with dichloromethane, then with 1% methanol in dichloromethane. The active fraction was flash chromatographed eluting with dichloromethane followed by 2% methanol in dichloromethane. The active fraction was evaporated and the residue triturated in dichloromethane/hexane giving 900 mg of the desired product, mp 121°-123° C.

Workup

  1. concentrationconcentrated to one-half its original volume and refrigerated overnight
  2. customThe solvent was removed
  3. dissolutionthe residue dissolved in dichloromethane
  4. washeluting first with dichloromethane
  5. customchromatographed
  6. washeluting with dichloromethane
  7. customThe active fraction was evaporated
  8. customthe residue triturated in dichloromethane/hexane giving 900 mg of the desired product, mp 121°-123° C.

Sources & evidence

ORD record
ord-dbaeee1d10774d5b9ecd93a63368c816
Source dataset
uspto-grants-1987_08
Patent number
US04686220

Reaction notes

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