3-(4-hydroxyphenyl)-N-benzylpropionamide → 4-(3-Benzylamino-propyl)-phenol

HRID 228156

Reaktionsgleichung

Reaktionsgleichung von HRID 228156
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([NH:14][C:15](=O)[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1>O1CCCC1>[CH2:7]([NH:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

5

Edukt 3

HCID 6204343-(4-hydroxyphenyl)-N-benzylpropionamideHCID 21226445Aluminium lithium hydrideHCID 68718528lithium aluminium hydride THF

Produkt 1

HCID 105380784-(3-Benzylamino-propyl)-phenolAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Add lithium aluminum hydride (8.00 g, 211 mmol) to anhydrous tetrahydrofuran (150 mL) and cool to 0° C. under nitrogen. Add N-benzyl-3-(4-hydroxy-phenyl)-propionamide (9.74 g, 38.2 mmol) to anhydrous tetrahydrofuran (80 mL) and add this solution slowly via cannula to the lithium aluminum hydride/tetrahydrofuran mixture at 0° C. under nitrogen. Once this addition is complete, remove the ice bath and heat to reflux for 18 h under nitrogen. Cool the reaction to 0° C. and slowly quench with water (200 mL). Adjust the pH of the solution to pH=8 with 4 M hydrochloric acid. Saturate this solution with sodium chloride, extract with ethyl acetate (3×100 mL), dry the extracts over magnesium sulfate, filter, and concentrate on a rotary evaporator to yield 9.00 g (98%) of 4-(3-benzylamino-propyl)-phenol: mass spectrum (ion spray): m/z=242.1 (M+1); 1H NMR (DMSO-d6): 7.31-7.16 (m, 6H), 6.95-6.92 (m, 2H), 6.66-6.62 (m, 2H), 3.65 (s, 2H), 2.48-2.43 (m, 5H), 1.68-1.60 (m, 2H).

Aufarbeitung

  1. additionOnce this addition
  2. customremove the ice bath
  3. temperatureheat
  4. temperatureto reflux for 18 h under nitrogen
  5. temperatureCool
  6. customthe reaction to 0° C.
  7. customslowly quench with water (200 mL)
  8. concentrationSaturate this solution with sodium chloride
  9. extractionextract with ethyl acetate (3×100 mL)
  10. dry with materialdry the extracts over magnesium sulfate
  11. filtrationfilter
  12. concentrationconcentrate on a rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-80b6ba78bdbc410297b771b9cbb71a98
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560463B2

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