1-Phenylpiperazine → HCID 178418617, Verbindung

HRID 5718

Reaktionsgleichung

Reaktionsgleichung von HRID 5718
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:29]([OH:31])=O)[CH2:13][C:14]1[N:18]=[CH:17][N:16](C(OCC2C=CC=CC=2)=O)[CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:32]1([N:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:29]([N:41]1[CH2:42][CH2:43][N:38]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:39][CH2:40]1)=[O:31])[CH2:13][C:14]1[N:18]=[CH:17][NH:16][CH:15]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 70961-PhenylpiperazineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 13141799Z-His(Z)-OH

Produkt 1

HCID 178418617HCID 178418617, VerbindungAusbeute 90,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

7.13 g of N,N'-dibenzyloxycarbonyl histidine, 3.00 g of 4-phenylpiperazine and 16.1 g of N-hydroxybenzotriazole were dissolved in 100 ml of tetrahydrofuran, and to the mixture was added 3.84 g of DCC (dicyclohexylcarbodiimide), and the whole was stirred at a room temperature for three hours. An insoluble matter was filtered off, the filtrate was concentrated under a reduced pressure, and to the concentrate was added 200 ml of ethyl acetate to reform crystals, which were then filtered off. The filtrate was sequentially washed with 20% potassium carbonate aqueous solution and saturated sodium chloride aqueous solution, dried over magnesium sulfate, and concentrated under a reduced pressure. The resulting residue was dissolved in 60 ml of methanol, and after an addition of a 10% ammonium-methanol solution and stirring at a room temperature for 30 minutes, the solution was concentrated under a reduced pressure to obtain a residue, which was then subjected to silica gel chromatography and eluted with chloroform/methanol (50:1 to 10:1) to obtain 6.61 g of the title compound in a colorless amorphous form.

Aufarbeitung

  1. filtrationAn insoluble matter was filtered off
  2. concentrationthe filtrate was concentrated under a reduced pressure
  3. additionto the concentrate was added 200 ml of ethyl acetate
  4. filtrationwere then filtered off
  5. washThe filtrate was sequentially washed with 20% potassium carbonate aqueous solution and saturated sodium chloride aqueous solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under a reduced pressure
  8. dissolutionThe resulting residue was dissolved in 60 ml of methanol
  9. additionafter an addition of a 10% ammonium-methanol solution
  10. stirringstirring at a room temperature for 30 minutes
  11. concentrationthe solution was concentrated under a reduced pressure
  12. customto obtain a residue, which
  13. washeluted with chloroform/methanol (50:1 to 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-12cc04c7756c400ea9f6a684f4b0a26c
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05245034

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