Diethyl Ether → 2-(3-Chlorophenyl)-3,5,5-trimethyl-2-morpholinol

HRID 650504

Reaktionsgleichung

Reaktionsgleichung von HRID 650504
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C@@:9]2([OH:18])[O:14][CH2:13][C:12]([CH3:16])([CH3:15])[NH:11][C@@H:10]2[CH3:17])[CH:6]=[CH:7][CH:8]=1.C(OCC)C.[OH-].[Na+]>O>[Cl:2][C:3]1[CH:4]=[C:5]([C:9]2([OH:18])[O:14][CH2:13][C:12]([CH3:15])([CH3:16])[NH:11][CH:10]2[CH3:17])[CH:6]=[CH:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 9943907Bupropion Morpholinol (2R,3R)-Isomer

Produkt 1

HCID 98379662-(3-Chlorophenyl)-3,5,5-trimethyl-2-morpholinol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

(+/−)-(2R*,3R*)-2-(3-chlorophenyl)-3,5,5-tiimethyl-2-morpholinol hydrochloride may be converted back to its free base by the following process. A 3.0 g sample of (+/−)-(2R*,3R*)-2-(3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol hydrochloride was dissolved in water (100 mL) and diethyl ether was added (200 mL). The mixture was chilled in an ice bath and the pH was adjusted to>10 with 1.0N aqueous sodium hydroxide. After stirring for 30 min., the phases were separated and the aqueous phase was extracted with diethyl ether. The combined diethyl ether extracts were dried (Na2SO4) and concentrated in vacuo to give 2.6 g of (+/−)-(2R*, 3R*)-2-(3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol as a white solid. This was used without further purification for the chiral chromatography described below.

Aufarbeitung

  1. temperatureThe mixture was chilled in an ice bath
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted with diethyl ether
  4. dry with materialThe combined diethyl ether extracts were dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-197ab059c1614a3483c1c1cc48389d32
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06274579B1

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