Benzaldehyde → 4-(2-(Benzylamino)ethyl)phenol

HRID 228143

Reaktionsgleichung

Reaktionsgleichung von HRID 228143
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.[BH4-].[Na+]>CO>[CH2:1]([NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 240BenzaldehydeHCID 5610TyramineHCID 4311764Sodium borohydride

Produkt 1

HCID 30425724-(2-(Benzylamino)ethyl)phenolAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Add benzaldehyde (7.5 mL, 74 mmol) to a stirred solution of tyramine (10.00 g, 73 mmol) and anhydrous methanol (90 mL). Heat reaction to reflux for 1 h under nitrogen. Cool reaction to 0° C. and slowly add sodium borohydride (2.84 g, 75 mmol). Stir for 1 h at room temperature and then concentrate on a rotary evaporator. Add water (100 mL) and stir for 1.5 h at room temperature. Filter and wash with water to yield 10.11 g (61%) of 4-(2-benzylamino-ethyl)-phenol: mass spectrum (ion spray): m/z=228.1 (M+1); 1H NMR (DMSO-d6): 9.14 (br s, 1H), 7.29-7.18 (m, 5H), 6.96 (d, 2H), 6.65 (d, 2H), 3.69 (s, 2H), 2.67-2.60 (m, 4H), 2.02 (br s, 1H).

Aufarbeitung

  1. temperatureHeat
  2. customreaction
  3. temperatureto reflux for 1 h under nitrogen
  4. temperatureCool
  5. customreaction to 0° C.
  6. concentrationconcentrate on a rotary evaporator
  7. stirringAdd water (100 mL) and stir for 1.5 h at room temperature
  8. filtrationFilter
  9. washwash with water

Quellen und Nachweise

ORD-Eintrag
ord-191aa0cde5924b54998f504420918901
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560463B2

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