Ethanol → N-[2-(4-Acetylphenyl)-1-methylethyl]-2-hydroxy-2-phenylethanamine

HRID 434364Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 434364
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](=O)[CH3:12])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH:14][CH:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:16][NH2:17].C(O)C>C1C=CC=CC=1.[Pt]=O>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([NH:17][CH2:16][CH:15]([OH:14])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:12])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 702EthanolHCID 1000PhenylethanolamineHCID 122541111-(4-Acetylphenyl) propan-2-one

Produkt 1

HCID 18627896N-[2-(4-Acetylphenyl)-1-methylethyl]-2-hydroxy-2-phenylethanamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 82844Platinum oxide (PtO)KatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

A mixture of 1-(4-acetylphenyl) propan-2-one (10.9 g) and 2-hydroxy-2-phenylethanamine (8.5 g) in benzene (200 ml) was refluxed for 4 hours under Dean and Stark conditions. The solvent was replaced with ethanol (200 ml), platinum oxide (200 mg) was added and the mixture was hydrogenated at ambient temperature and pressure for 6 hours. The solution was filtered and the filtrate was evaporated and chromatographed on silica gel 60 (400 g) eluting with 1% methanol/chloroform. The first fraction (9.0 g) was crystallised from ether to give the title compound as a 9:91 mixture of diasteroisomers m.p. 120°-135°.

Aufarbeitung

  1. temperaturewas refluxed for 4 hours under Dean and Stark conditions
  2. additionwas added
  3. customwas hydrogenated at ambient temperature
  4. filtrationThe solution was filtered
  5. customthe filtrate was evaporated
  6. customchromatographed on silica gel 60 (400 g)
  7. washeluting with 1% methanol/chloroform
  8. customThe first fraction (9.0 g) was crystallised from ether

Quellen und Nachweise

ORD-Eintrag
ord-541523cccbff4fa2a34e96a373f22372
Quelldatensatz
uspto-grants-1983_08
Patentnummer
US04396627

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