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 1370190Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1370190
[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.[CH2:27]([O:29][C:30](=[O:35])[CH:31](Br)[CH2:32][CH3:33])[CH3:28].C([O-])([O-])=O.[Na+].[Na+].O>CN1CCCC1=O>[CH2:32]([CH:31]([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:30]([O:29][CH2:27][CH3:28])=[O:35])[CH3:33]

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-dihydro4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-3H-1,2,4-triazol-3-one (0.05 mol), 2-bromo-butanoic acid ethyl ester (0.055 mol) and Na2CO3 (0.15 mol) in 1-methyl-2-pyrrolidinone (250 m1) was stirred at 75° C. over 2-Bromobutanoic acid ethyl ester (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 diisopropylether and ethylacetate, 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. 1).

Aufarbeitung

  1. additionwas added again
  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 diisopropylether
  10. filtrationethylacetate, filtered off
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-fde87d052fcd41cfabb56f9126bc05af
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06583136B1

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