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

HRID 228175

Reaktionsgleichung

Reaktionsgleichung von HRID 228175
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[BH4-].[Na+]>CO>[CH2:11]([NH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 240BenzaldehydeHCID 5610TyramineHCID 4311764Sodium borohydride

Produkt 1

HCID 30425724-(2-(Benzylamino)ethyl)phenolAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Combine tyramine (5.0 g, 36.4 mmol), benzaldehyde (3.8 ml, 37.2 mmol) in MeOH (46 mL), heat at reflux for 2 h. Cool the mixture at 0° C. and add NaBH4 (1.44 g, 38.2 mmol). Stir at room temperature overnight. Remove most of MeOH, add H2O and stir for 2 h. Filter the mixture and wash the white solid with water. Dry the solid precipitate under vacuum at 40° C. overnight to afford the title compound (7.53 g, 91%). Electrospray MS M+1 ion=228. 1H-NMR (methanol-d4, 300 MHz): 7.40-7.20 (m, 5H), 7.03-6.95 (m, 2H), 6.73-6.65 (m, 2H), 3.75 (s, 2H), 2.85-2.65 (m, 4H).

Aufarbeitung

  1. temperatureat reflux for 2 h
  2. customRemove most of MeOH
  3. additionadd H2O
  4. stirringstir for 2 h
  5. filtrationFilter the mixture
  6. washwash the white solid with water
  7. customDry the solid precipitate under vacuum at 40° C. overnight

Quellen und Nachweise

ORD-Eintrag
ord-0dbd6b1b80d545b78095c09f997a45de
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560463B2

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