Dichloromethane → 3,4-Dihydroisoquinoline

HRID 1900542

Reaktionsgleichung

Reaktionsgleichung von HRID 1900542
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.C(Cl)Cl.S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].[OH-].[Na+]>O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Ni+2]>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]=1

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 70461,2,3,4-TetrahydroisoquinolineHCID 14798Sodium HydroxideHCID 24412Potassium Persulfate

Produkt 1

HCID 767053,4-Dihydroisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5284429Nickel sulfate hexahydrateKatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

Into a 5000 ml, 3-neck round-bottom flask equipped with a mechanical stirrer is placed 1,2,3,4-tetrahydroisoquinoline (1) (25.005 g) and methylene chloride (750 ml). A solution of potassium persulfate (71.376 g) and sodium hydroxide (18.0456 g) in deionized water (1650 ml) is added. While vigorously stirring the biphasic mixture, a solution of nickel sulfate hexahydrate (0.6499 g) in deionized water (75 ml) is added dropwise to the mixture. The reaction is allowed to stir overnight at room temperature. The biphasic mixture is vacuum filtered through Celite, the phases separated and the water layer extracted (3×300 ml) with methylene chloride. The organics are combined, dried with MgSO4 and reduced by rotary evaporation to a thick, dark brown oil. The desired product is isolated from the oil by Kugelrohr distillation (0.1 mm Hg, 75° C.). The preparation is represented by the following reaction: ##STR26##

Aufarbeitung

  1. customInto a 5000 ml, 3-neck round-bottom flask equipped with a mechanical stirrer
  2. stirringto stir overnight at room temperature
  3. filtrationfiltered through Celite
  4. customthe phases separated
  5. extractionthe water layer extracted (3×300 ml) with methylene chloride
  6. dry with materialdried with MgSO4
  7. customreduced by rotary evaporation to a thick, dark brown oil

Quellen und Nachweise

ORD-Eintrag
ord-1ef48c0ba78547a19b220b759a7f2b3e
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05576282

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