Benzylamine → 3-(4-hydroxyphenyl)-N-benzylpropionamide

HRID 492312

Reaktionsgleichung

Reaktionsgleichung von HRID 492312
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18](OC)=[O:19])=[CH:12][CH:11]=1>Cl>[CH2:1]([NH:8][C:18](=[O:19])[CH2:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([OH:9])=[CH:11][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 7504BenzylamineHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl ester

Produkt 1

HCID 6204343-(4-hydroxyphenyl)-N-benzylpropionamideAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

Add benzylamine (32.0 mL, 293 mmol) to methyl 3-(4-hydroxyphenyl)propionate (7.01 g, 38.9 mmol) and heat to 150° C. for 18 h under nitrogen. Cool to room temperature and pour the reaction mixture into 5 N hydrochloric acid (200 mL) and extract with ethyl acetate (3× 150 mL). Wash the ethyl acetate extracts with 5 N hydrochloric acid (200 mL), dry the extracts over magnesium sulfate, filter, and concentrate on a rotary evaporator to yield 9.74 g (98%) of N-benzyl-3-(4-hydroxy-phenyl)-propionamide: mass spectrum (ion spray): m/z=256.2 (M+1); 1H NMR (DMSO-d6): 9.15 (s, 1H), 8.28 (t, 1H), 7.39-6.96 (m, 7H), 6.66-6.63 (m, 2H), 4.23 (d, 2H), 2.72 (t, 2H), 2.37 (t, 2H).

Aufarbeitung

  1. temperatureCool to room temperature
  2. extractionextract with ethyl acetate (3× 150 mL)
  3. washWash the ethyl acetate
  4. dry with materialdry the extracts over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate on a rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-5ffd4ae524054cf5a8947fc06e48d9d3
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531557B2

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