Toluene → 4-Benzyloxycarbonyl-1-[4-(4-pyridyl)benzyl]-2-piperazinone

HRID 2186123Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2186123
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21](Br)=[CH:20][CH:19]=2)[C:13](=[O:25])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:26]1[CH:31]=[CH:30][C:29](OB(O)O)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>C(OCC)(=O)C.C(O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:29]3[CH:30]=[CH:31][N:26]=[CH:27][CH:28]=3)=[CH:20][CH:19]=2)[C:13](=[O:25])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 218058124-Pyridylboric acidHCID 23447549Benzyl 4-[(4-bromophenyl)methyl]-3-oxopiperazine-1-carboxylate

Produkt 1

HCID 234475764-Benzyloxycarbonyl-1-[4-(4-pyridyl)benzyl]-2-piperazinoneAusbeute 40,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 4-benzyloxycarbonyl-1-(4-bromobenzyl)-2-piperazinone (807 mg), 4-pyridylboric acid (244 mg), tetrakis (triphenylphosphine)palladium (69 mg), 2M sodium carbonate solution (2 ml), toluene (8 ml) and ethanol (2 ml) was refluxed overnight. After the mixture was cooled, ethyl acetate was added to the reaction solution. The mixture was washed with water and saturated brine, dried (MgSO4) and concentrated. The residue was purified with silica gel column chromatography (ethyl acetate) to give colorless crystals of the title compound (283 mg).

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. temperatureAfter the mixture was cooled
  3. washThe mixture was washed with water and saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel column chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-b859f5886bf84ecba8582f55bb81db30
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06403595B1

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