Water → 3-[2-[4-(2-Methoxyphenyl)-1-piperazinyl]ethyl]-2,4(1H,3H)-quinazolinedione

HRID 483233

Reaction equation

HRID 483233 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][NH:17][C:18](=[O:26])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[NH2:25])[CH2:11][CH2:10]1.N[C:28](N)=[O:29].O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]2[C:18](=[O:26])[C:19]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:25][C:28]2=[O:29])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 1176UreaHCID 132291672-Amino-N-{2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl}benzamide

Product 1

HCID 1220653-[2-[4-(2-Methoxyphenyl)-1-piperazinyl]ethyl]-2,4(1H,3H)-quinazolinedioneYield 92.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(2-Methoxyphenyl)-4-[2-(2-aminobenzoyl)aminoethyl]piperazine (3.54 g) and urea (1.2 g) were dissolved in dimethylformamide (20 ml) and the resulting solution was heated at an external temperature of 140° to 180° C. for 5 to 8 hours. After completion of the reaction, water (200 ml) was added to the reaction mixture and the resulting crystal was filtered off. Upon recrystallization from dioxane, 3-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]2,4-(1H,3H)-quinazolinedione (3.5 g) was obtained as needles. Its physicochemical data was the same as that of the product obtained in (a).

Workup

  1. temperaturethe resulting solution was heated at an external temperature of 140° to 180° C. for 5 to 8 hours
  2. additionwas added to the reaction mixture
  3. filtrationthe resulting crystal was filtered off
  4. customUpon recrystallization from dioxane

Sources & evidence

ORD record
ord-fa6f930c11a843969a837ae56f8048bd
Source dataset
uspto-grants-1986_03
Patent number
US04578465

Linked notes

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