Triethylamine → 1-(3-Acetylaminobenzoyl)-4-[2-(4-chlorophenyl)ethyl]piperazine

HRID 1381884

Reaktionsgleichung

Reaktionsgleichung von HRID 1381884
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=O)(=[O:3])[CH3:2].C(N(CC)CC)C.C(OC(Cl)=O)C.[Cl:27][C:28]1[CH:41]=[CH:40][C:31]([CH2:32][CH2:33][N:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)=[CH:30][CH:29]=1>CN(C=O)C.C(Cl)Cl>[Cl:27][C:28]1[CH:41]=[CH:40][C:31]([CH2:32][CH2:33][N:34]2[CH2:35][CH2:36][N:37]([C:8](=[O:10])[C:7]3[CH:11]=[CH:12][CH:13]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:6]=3)[CH2:38][CH2:39]2)=[CH:30][CH:29]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 488473-Acetamidobenzoic acidHCID 122357141-[2-(4-Chlorophenyl)ethyl]piperazine

Produkt 1

HCID 190995361-(3-Acetylaminobenzoyl)-4-[2-(4-chlorophenyl)ethyl]piperazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

10 g of 3-acetamidobenzoic acid are dissolved in 100 ml of DMF. At a temperature of from -5° to 0° there are added dropwise, while stirring, firstly 5.65 g of triethylamine and then 6.05 g of chloroformic acid ethyl ester dissolved in 40 ml of CH2Cl2. The whole is stirred for a further 30 minutes at from 0° to +5° and then, at the same temperature, 12.54 g of 1-(p-chlorophenethyl)piperazine in 75 ml of DMF are added dropwise. The whole is stirred overnight at room temperature and then concentrated to dryness by evaporation. The residue is taken up in 350 ml of CH2Cl2 and the whole is washed with 150 ml of 2N NaOH and with 50 ml of H2O and dried over Na2SO4. After filtration and concentration by evaporation, a brown oil is obtained, which is caused to crystallise with ether. Recrystallisation is effected from ethanol/ether. 1-[2-(p-chlorophenyl)-ethyl]-4-(3-acetamidobenzoyl)-piperazine having a melting point of 101°-107° is thus obtained.

Aufarbeitung

  1. additionAt a temperature of from -5° to 0° there are added dropwise
  2. stirringThe whole is stirred for a further 30 minutes at from 0° to +5°
  3. stirringThe whole is stirred overnight at room temperature
  4. concentrationconcentrated to dryness by evaporation
  5. washthe whole is washed with 150 ml of 2N NaOH and with 50 ml of H2O
  6. dry with materialdried over Na2SO4
  7. filtrationAfter filtration and concentration
  8. customby evaporation
  9. customa brown oil is obtained
  10. customto crystallise with ether
  11. customRecrystallisation

Quellen und Nachweise

ORD-Eintrag
ord-93c2324ff7574cbdb668543b2741734c
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04804661

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