Water → (+/-)-ethyl alpha-ethyl-4,5-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-5-oxo-1H-1,2,4-triazol-1-acetate

HRID 1934581Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1934581
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH:25]=[N:24][NH:23][C:22]4=[O:26])=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Br[CH:28]([CH2:34][CH3:35])[C:29]([O:31][CH2:32][CH3:33])=[O:30].C([O-])([O-])=O.[Na+].[Na+].O>CN1CCCC1=O>[CH2:34]([CH:28]([N:23]1[C:22](=[O:26])[N:21]([C:18]2[CH:19]=[CH:20][C:15]([N:12]3[CH2:11][CH2:10][N:9]([C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[CH2:14][CH2:13]3)=[CH:16][CH:17]=2)[CH:25]=[N:24]1)[C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH3:35]

Komponenten

6

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 79039Butanoic acid, 2-bromo-, ethyl ester2×HCID 42465972,4-Dihydro-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-3H-1,2,4-triazol-3-one

Produkt 1

HCID 86758049(+/-)-ethyl alpha-ethyl-4,5-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-5-oxo-1H-1,2,4-triazol-1-acetateAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A mixture of 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-3H-1,2,4-triazol-3-one (0.05 mol), ethyl 2-bromobutanoate (0.055 mol) and Na2CO3 (0.15 mol) in 1-methyl-2-pyrrolidinone (250 ml) was stirred at 75° C. overnight. Ethyl 2-bromobutanoate (0.015 mol) was added again. The mixture was stirred at 75° C. for 6 hours, at room temperature for 48 hours, poured out into H2O and stirred for 30 minutes. The precipitate was filtered off and dissolved in CH2Cl2. The solution was filtered. The filtrate was dried, filtered and the solvent was evaporated. The residue was triturated in DIPE and ethyl acetate, filtered off and dried, yielding 10 g (43%) of (±)-ethyl α-ethyl-4,5-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-5-oxo-1H-1,2,4-triazol-1-acetate (interm. 9).

Aufarbeitung

  1. stirringThe mixture was stirred at 75° C. for 6 hours, at room temperature for 48 hours
  2. stirringstirred for 30 minutes
  3. filtrationThe precipitate was filtered off
  4. dissolutiondissolved in CH2Cl2
  5. filtrationThe solution was filtered
  6. customThe filtrate was dried
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was triturated in DIPE and ethyl acetate
  10. filtrationfiltered off
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-98c8d9cf4a7b4e279a97bfbdcd5f6214
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06384030B1

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