Benzylamine → N-Benzyl-1-(4-methoxyphenyl)propan-2-amine (S)-2-hydroxy-2-phenylacetate

HRID 1739127Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1739127
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=O)[CH3:11])=[CH:5][CH:4]=1.[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[H][H].[C:23]([OH:33])(=[O:32])[C@H:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[OH:25]>[Pt].CO>[C:23]([OH:33])(=[O:32])[C@H:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[OH:25].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([CH3:11])[NH:20][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:5][CH:4]=1

Komponenten

7

Edukt 4

HCID 7504BenzylamineHCID 312311-(p-Methoxyphenyl)-2-propanoneHCID 439616(S)-mandelic acidHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 71721458N-Benzyl-1-(4-methoxyphenyl)propan-2-amine (S)-2-hydroxy-2-phenylacetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23939PlatinumKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To 800 mL of methanol were added 328 g of 4-methoxyphenylacetone (2 mol) and 214 g of N-benzylamine (2 mol). The imine formation was exothermic and the solution warmed to 45° C. After reaction was complete, the solution was hydrogenated at 50 psi for 6-8 hours in the presence of 3.3 g of 5% platinum on carbon catalyst. When the hydrogen uptake had stopped, the reaction was filtered through diatomaceous earth, and the filter cake was washed with 200 mL of methanol. The combined filtrates were placed in a 6-liter flask and diluted with 4.2 liters of methanol. (S)-L-Mandelic acid (304 g, 2 mol) was added and the mixture heated with stirring to reflux to obtain a clear solution. The solution was cooled to room temperature, stirred at room temperature for two hours and the mandelic acid salt filtered off. The recrystallization was repeated three times to obtain 60-70 g of the mandelic acid salt of the benzyl amine having an isomeric purity greater than 99.8% and a melting point of 164° C.

Aufarbeitung

  1. customAfter reaction
  2. filtrationthe reaction was filtered through diatomaceous earth
  3. washthe filter cake was washed with 200 mL of methanol
  4. customThe combined filtrates were placed in a 6-liter flask
  5. additiondiluted with 4.2 liters of methanol
  6. temperaturethe mixture heated
  7. temperatureto reflux
  8. customto obtain a clear solution
  9. temperatureThe solution was cooled to room temperature
  10. stirringstirred at room temperature for two hours
  11. filtrationthe mandelic acid salt filtered off
  12. customThe recrystallization

Quellen und Nachweise

ORD-Eintrag
ord-f877b2847e9b4088b7e2a369b567e8de
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05965622

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