1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-(4-Phthalimidobutyloxy)pyridine

HRID 6139

Reaktionsgleichung

Reaktionsgleichung von HRID 6139
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.Br[CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23].C1CCN2C(=NCCC2)CC1>CN(C=O)C>[C:14]1(=[O:23])[N:13]([CH2:12][CH2:11][CH2:10][CH2:9][O:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]12

Komponenten

5

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 93575N-(4-Bromobutyl)phthalimideHCID 178418642HCID 178418642, Verbindung

Produkt 1

HCID 190791584-(4-Phthalimidobutyloxy)pyridineAusbeute 17,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4.76 g (50 mmol) of 4-hydroxypyridine and 15.52 g (55 mmol) of N-(4bromobutyl)phthalimide in 80 ml of DMF was added 8.23 ml (5 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene. The mixture was stirred at room temperature for 7 hours. After the solvent was distilled off, the mixture was poured into water and extracted with ethyl acetate. The mixture was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain 2.63 g of the desired compound (yield: 17.2%, colorless crystals).

Aufarbeitung

  1. distillationAfter the solvent was distilled off
  2. additionthe mixture was poured into water
  3. extractionextracted with ethyl acetate
  4. washThe mixture was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was purified by column chromatography (eluent: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-8ddd5dd4e0684c5fbacd7457ef7264ca
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246948

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