N,N-Dimethylethylenediamine → Ammonia

HRID 1766056Notes

Reaction equation

HRID 1766056 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-16db98826cac49ef82ba4d5e514ac56b
Source dataset
uspto-grants-2007_06
Patent number
US07230000B1

Reaction notes

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