Hydrochloric Acid → HCID 136359214, Verbindung

HRID 1153959

Reaktionsgleichung

Reaktionsgleichung von HRID 1153959
C(=O)([O-])[O-].[K+].[K+].[Cl:7]C1C=C(N2CCN(C[CH2:21][CH2:22][N:23]3[C:27](=[O:28])[N:26]=[C:25](CC)[NH:24]3)CC2)C=CC=1.[O:31](CCBr)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[I-].[K+].ClC1C=C(N2CCN(CCCN3C(=O)N(CCOC4C=CC=CC=4)C(CC)=N3)CC2)C=CC=1.Cl>C(#N)C.C(O)C>[ClH:7].[O:31]([CH2:21][CH2:22][N:23]1[C:27](=[O:28])[NH:26][CH:25]=[N:24]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 4449NefazodoneHCID 4875Potassium IodideHCID 11430Potassium Carbonate2×HCID 68526Benzene, (2-bromoethoxy)-HCID 178437794HCID 178437794, Verbindung

Produkt 1

HCID 136359214HCID 136359214, VerbindungAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

Reaction in Acetonitrile With Potassium Carbonate. A mixture of 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-1H-1,2,4-triazol-3(2H)-one (15 g., 0.043 mole), phenoxyethyl bromide (8.62 g., 0.043 mole), potassium carbonate (11.9 g., 0.086 mole) and a trace of potassium iodide in 100 ml. of acetonitrile is refluxed for a 64 hr. period. The reaction mixture is filtered, the filtrate concentrated under reduced pressure and residual material taken up in ether and filtered. Concentration of the ethereal filtrate affords 18.35 g. (91%) of the free base product 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-4-(2-phenoxyethyl)-2H-1,2,4-triazol-3(4h)-one. The free base is converted to the hydrochloride in ethanol employing ethanolic hydrogenchloride and crystallized from ethanol to afford a 53% yield of analytically pure 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-4-(2 -phenoxyethyl-2H-1,2,4-triazol-3(4H)-one hydrochloride, m.p. 175°-177° C.

Aufarbeitung

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate concentrated under reduced pressure and residual material
  3. filtrationfiltered
  4. customConcentration of the ethereal filtrate affords 18.35 g
  5. customcrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-c3c42eef760742febe035aae7ba031d4
Quelldatensatz
uspto-grants-1984_12
Patentnummer
US04487773

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