N,N-Dimethylethylenediamine → HCID 86740997, compound

HRID 64905Notes

Reaction equation

HRID 64905 reaction equation
Br[CH:2]1[CH2:19][CH:18]([OH:20])[CH2:17][C:16]2[CH:15]=[C:14]3[C:5]([C:6](=[O:28])[C:7]4[CH:8]=[CH:9][CH:10]([CH2:26][CH3:27])[C:11]5([O:25][CH2:24][CH2:23][O:22]5)[C:12]=4[C:13]3=[O:21])=[C:4]([OH:29])[C:3]1=2.[CH3:30][N:31]([CH3:35])[CH2:32][CH2:33][NH2:34]>>[CH3:30][N:31]([CH3:35])[CH2:32][CH2:33][NH:34][CH:2]1[CH2:19][CH:18]([OH:20])[CH2:17][C:16]2[CH:15]=[C:14]3[C:5]([C:6](=[O:28])[C:7]4[CH:8]=[CH:9][CH:10]([CH2:26][CH3:27])[C:11]5([O:25][CH2:24][CH2:23][O:22]5)[C:12]=4[C:13]3=[O:21])=[C:4]([OH:29])[C:3]1=2

Participants

3

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 867409987-Bromo-9-(1,1-ethylenedioxy)ethyl-6,9-dihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione

Product 1

HCID 86740997HCID 86740997, compound

Procedure

7-Bromo-9-(1,1-ethylenedioxy)ethyl-6,9-dihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione (571 mg) prepared in the foregoing step and N,N-dimethylethylenediamine (10 ml) were subjected to reaction in a nitrogen stream while cooling with ice for 1 hour. Excess of the N,N-dimethylethylenediamine was eliminated by distillation under reduced pressure. The residue was dissolved in dichloromethane (2 ml) and ether (4 ml) was added thereto, whereby 7-(2-dimethylaminoethyl)amino-9-(1,1-ethylenedioxy)ethyl-6,9-dihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione was obtained as yellow crystals (124 mg). M.P., 192°-196° C.

Workup

  1. customwere subjected to reaction in a nitrogen stream
  2. temperaturewhile cooling with ice for 1 hour
  3. distillationExcess of the N,N-dimethylethylenediamine was eliminated by distillation under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane (2 ml)
  5. additionether (4 ml) was added

Sources & evidence

ORD record
ord-b6c8efad8670450aa6da9f9972705cd9
Source dataset
uspto-grants-1986_09
Patent number
US04610986

Reaction notes

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