Dimepranol → 1-(Dimethylamino)-2-propyl Isopropyl-(4-chlorophenyl)acetate

HRID 464149

Reaktionsgleichung

Reaktionsgleichung von HRID 464149
[CH3:1][N:2]([CH3:7])[CH2:3][CH:4]([OH:6])[CH3:5].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH:18]([CH3:20])[CH3:19])=[C:16]=[O:17])=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[CH:18]([CH:15]([C:12]1[CH:13]=[CH:14][C:9]([Cl:8])=[CH:10][CH:11]=1)[C:16]([O:6][CH:4]([CH3:5])[CH2:3][N:2]([CH3:7])[CH3:1])=[O:17])([CH3:20])[CH3:19]

Komponenten

4

Edukt 2

HCID 37511DimepranolHCID 11019754(4-Chlorophenyl)isopropylketene

Produkt 1

HCID 541300301-(Dimethylamino)-2-propyl Isopropyl-(4-chlorophenyl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A 1 dram vial fitted with a septum cap was charged with 0.69 g of toluene followed by 1.08 g of optically-active 1-(dimethylamino)-2-propanol. The resulting mixture was chilled with ice and then 0.196 g of (4-chlorophenyl)isopropylketene was injected. The reaction temperature rose slowly to 30° C. The color discharged after 1.25 hours at room temperature. The reaction product was separated by gas liquid chromatography to give the desired product in a diastereomer ratio of 25.6% of isomer pair 1 and 74.4% of isomer pair 2.

Aufarbeitung

  1. customA 1 dram vial fitted with a septum
  2. customcap
  3. temperatureThe resulting mixture was chilled with ice
  4. customrose slowly to 30° C
  5. customThe reaction product was separated by gas liquid chromatography

Quellen und Nachweise

ORD-Eintrag
ord-87fded12506a43bda6ba40cbf9e52f2a
Quelldatensatz
uspto-grants-1985_10
Patentnummer
US04546198

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