Triethylamine → 2-(4-Ethoxycarbonylpiperidino)-4-(3,4-methylenedioxy-benzyl)amino-6-chloroquinazoline

HRID 1900686Notes

Reaction equation

HRID 1900686 reaction equation
[NH:1]1[CH2:10][CH2:9][CH:4]([C:5]([O:7][CH3:8])=[O:6])[CH2:3][CH2:2]1.[CH2:11](N(CC)CC)C.Cl[C:19]1[N:28]=[C:27]([NH:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]3[O:37][CH2:38][O:39][C:33]=3[CH:32]=2)[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([Cl:40])[CH:25]=2)[N:20]=1>CC(O)C>[CH2:8]([O:7][C:5]([CH:4]1[CH2:9][CH2:10][N:1]([C:19]2[N:28]=[C:27]([NH:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]4[O:37][CH2:38][O:39][C:33]=4[CH:32]=3)[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([Cl:40])[CH:25]=3)[N:20]=2)[CH2:2][CH2:3]1)=[O:6])[CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 424914Methyl isonipecotateHCID 22339865HCID 22339865, compound

Product 1

HCID 211838922-(4-Ethoxycarbonylpiperidino)-4-(3,4-methylenedioxy-benzyl)amino-6-chloroquinazolineYield 97.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

3.61 g of methyl isonipecotate, 2.32 g of triethylamine and 5 ml of 2-propanol were added to 1 g of 2,6-dichloro-4-(3,4-methylenedioxybenzyl)aminoquinazoline prepared in Example 92. The obtained mixture was refluxed for 100 minutes. The mixture thus obtained was extracted with chloroform twice. The organic layers were combined, washed with water, dried over magnesium sulfate and freed from the solvent by distillation. The residue was recrystallized (from ethanol/water) to give 1.31 g of the title compound.

Workup

  1. temperatureThe obtained mixture was refluxed for 100 minutes
  2. customThe mixture thus obtained
  3. extractionwas extracted with chloroform twice
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationfreed from the solvent by distillation
  7. customThe residue was recrystallized (from ethanol/water)

Sources & evidence

ORD record
ord-19d7f9603d6342a1b98cc768b37f709a
Source dataset
uspto-grants-1996_11
Patent number
US05576322

Reaction notes

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