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

HRID 483232

Reaktionsgleichung

Reaktionsgleichung von HRID 483232
[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][CH:16]([NH2:26])C(=O)C2C=CC=CC=2N)[CH2:11][CH2:10]1.C([N:29]([CH2:32][CH3:33])CC)C.ClC([O:37][C:38](Cl)(Cl)Cl)=O.[C:42](=[O:45])([O-])O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][N:26]2[C:42](=[O:45])[C:33]3[C:32](=[CH:8][CH:3]=[CH:4][CH:5]=3)[NH:29][C:38]2=[O:37])[CH2:13][CH2:14]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 516892Sodium BicarbonateHCID 571547151-(2-Methoxyphenyl)-4-[2-(2-aminobenzoyl)-aminoethyl]piperazine

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of 1-(2-methoxyphenyl)-4-[2-(2-aminobenzoyl)-aminoethyl]piperazine (3.54 g) and triethylamine (2.2 g) was dissolved in methylene chloride (50 ml), and the resulting solution was added dropwise to a solution of trichloromethyl chloroformate (0.989 g) in methylene chloride (20 ml) under stirring at between -5° and 5° C. Then, the mixture was gradually heated to room temperature at which it was held for 1 to 2 hours to effect reaction. After completion of the reaction, saturated aqueous sodium hydrogencarbonate was added to the reaction mixture and the resulting mixture was extracted with methylene chloride, the methylene chloride layer was washed with water twice and dried on anhydrous magnesium sulfate. The solvent was concentrated under vacuum and isopropanol was added to the residue to give 2.28 g of crystalline 3-[2-[4-(2-methoxyphenyl)-1-piperazinyl]-ethyl]-2,4-(1H,3H)quinazolinedione having a melting point of 217°-218° C. (recrystallized from chloroform-ether).

Aufarbeitung

  1. customreaction
  2. additionwas added to the reaction mixture
  3. extractionthe resulting mixture was extracted with methylene chloride
  4. washthe methylene chloride layer was washed with water twice
  5. dry with materialdried on anhydrous magnesium sulfate
  6. concentrationThe solvent was concentrated under vacuum and isopropanol
  7. additionwas added to the residue

Quellen und Nachweise

ORD-Eintrag
ord-62a9f048b6a045bdbc15ff6899d92e73
Quelldatensatz
uspto-grants-1986_03
Patentnummer
US04578465

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