Water → 4-Phenoxybutan-1-amine

HRID 2421956Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2421956
[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][N:12]1C(=O)C2C(=CC=CC=2)C1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN.O.CCOC(C)=O>CCO>[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 9321HydrazineHCID 166375972-(4-Phenoxybutyl)-1H-isoindole-1,3(2H)-dione

Produkt 1

HCID 1162404-Phenoxybutan-1-amineAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2-(4-phenoxybutyl)1H-isoindole-1,3(2H)-dione (10.10 g, 3.27 mmol) and 25% hydrazine solution in water (2.88 ml, 13.10 mmol) in EtOH (30 ml) was warmed at reflux. After 1.5 h, EtOAc was added and the mixture was extracted with brine. The combined aqueous phases were then re-extracted with EtOAc and all the organic phases combined. These were then extracted with 1N HCl, the acidic aqueous phases combined, basified with 2N NaOH and re-extracted into EtOAc before evaporating to dryness to give the title compound (0.411 mg, 67%) as an oil. 1H NMR (500 MHz CDCl3): δ 7.32-2.26 (m, 2H), 6.95 (t, 1H), 4.00 (t, 2H), 2.80 (t, 2H), 1.90-1.82 (m, 2H), 1.68-1.62 (m, 2H).

Aufarbeitung

  1. temperaturewas warmed
  2. temperatureat reflux
  3. extractionthe mixture was extracted with brine
  4. extractionThe combined aqueous phases were then re-extracted with EtOAc and all the organic phases
  5. extractionThese were then extracted with 1N HCl
  6. extractionre-extracted into EtOAc
  7. custombefore evaporating to dryness

Quellen und Nachweise

ORD-Eintrag
ord-3e32c09772a5498ab7fd2c1babc4d3c2
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960380B2

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