N,N-Dimethylethylenediamine → Ammonia

HRID 732969Notes

Reaction equation

HRID 732969 reaction equation
[Br:1][CH:2]([C:5]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13](=[O:22])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1)[CH2:3][CH3:4].CN(C)CCN>C(O)C>[NH3:6].[Br:1][CH:2]([C:5]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13](=[O:22])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1)[CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 21958885HCID 21958885, compound

Product 2

HCID 222AmmoniaHCID 21958885HCID 21958885, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 5 (10.7 g, 0.03 mole) and N,N-dimethylethylenediamine (6.6 mL, 0.06 mole) were dissolved in abs. ethanol (60 mL) and heated at reflux for 6 h. After completion of the reaction, the solvent was evaporated under reduced pressure. The residue was dissolved in dichloromethane (150 mL) and washed with 3% aq. NaOH solution (ca. 10-20 mL). The organic layer was dried over MgSO4 and evaporated to dryness under reduced pressure. The remaining oily product was purified by flash chromatography on a short silica gel pad using an eluent of CHCl3-MeOH-aq.NH3, 90:10:0.1, to give the desired compound (5), 2-[1′-(N,N-dimethylethylenediamino)propyl]-3-benzylquinazolin-4-one (6) (6.0 g, 55%).

Workup

  1. temperatureat reflux for 6 h
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane (150 mL)
  5. washwashed with 3% aq. NaOH solution (ca. 10-20 mL)
  6. dry with materialThe organic layer was dried over MgSO4
  7. customevaporated to dryness under reduced pressure
  8. customThe remaining oily product was purified by flash chromatography on a short silica gel pad

Sources & evidence

ORD record
ord-8e738d085e454a4eaf1163de4a12dd9d
Source dataset
uspto-grants-2009_09
Patent number
US07589098B2

Reaction notes

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