Epichlorohydrin → 6-(2,3-Epoxy-propoxy)-2-formyl-1,2,3,4-tetrahydroisoquinoline

HRID 597208Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 597208
[OH-].[Na+].[CH:3]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:15])[CH:11]=2)[CH2:6]1)=[O:4].[CH2:16]([CH:18]1[O:20][CH2:19]1)Cl>O>[O:20]1[CH2:19][CH:18]1[CH2:16][O:15][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH2:6][N:5]([CH:3]=[O:4])[CH2:14][CH2:13]2

Komponenten

5

Edukt 3

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 214470386-Hydroxy-3,4-dihydroisoquinoline-2(1H)-carbaldehyde

Produkt 1

HCID 214470066-(2,3-Epoxy-propoxy)-2-formyl-1,2,3,4-tetrahydroisoquinolineAusbeute 82,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 6.8 g of sodium hydroxide in 90 ml of water is added dropwise over 1 hour to a mixture of 26.6 g of 2-formyl-1,2,3,4-tetrahydro-6-hydroxy-isoquinoline and 42.5 g of epichlorohydrin at 60° C. The reaction mixture is held at this temperature for an additional hour, then allowed to cool and extracted several times with methylene chloride. The organic phase, dried over sodium sulfate, is evaporated and the residue is rubbed with diethyl ether. 29.0 g of 6-(2,3-epoxy-propoxy)-2-formyl-1,2,3,4-tetrahydro isoquinoline are obtained. m.p. = 78° - 79° C. (ethyl acetate - diethyl ether).

Aufarbeitung

  1. waitThe reaction mixture is held at this temperature for an additional hour
  2. temperatureto cool
  3. extractionextracted several times with methylene chloride
  4. dry with materialThe organic phase, dried over sodium sulfate
  5. customis evaporated

Quellen und Nachweise

ORD-Eintrag
ord-3c13fef567cf42eabfbe987643084982
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04013663

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