Water → 2-[4-(Dipropylamino)butyl]-1,2,3,4-tetrahydro-6-isoquinolinecarboaldehyde

HRID 68639Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 68639
[CH2:1]([N:4]([CH2:21][CH2:22][CH3:23])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][OH:20])[CH:15]=2)[CH2:10]1)[CH2:2][CH3:3].C(N(CC)CC)C.O>CS(C)=O>[CH2:21]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH:19]=[O:20])[CH:15]=2)[CH2:10]1)[CH2:22][CH3:23]

Komponenten

5

Edukt 3

HCID 962WaterHCID 8471TriethylamineHCID 67164894HCID 67164894, Verbindung

Produkt 1

HCID 866542922-[4-(Dipropylamino)butyl]-1,2,3,4-tetrahydro-6-isoquinolinecarboaldehydeAusbeute 99,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of the compound 21 (2.28 g) and triethylamine (4.99 mL) in dimethyl sulfoxide (30 mL), a sulfur trioxide-pyridine complex (2.28 g) was slowly added. The reaction mixture was stirred at room temperature for one hour. To the reaction solution, water (100 mL) was added. The aqueous layer was extracted twice with dichloromethane (50 mL). The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by silica gel chromatography (ethyl acetate:methanol:triethylamine=10:1:0→10:1:0.5) to obtain the title compound (2.26 g) having the following physical properties.

Aufarbeitung

  1. extractionThe aqueous layer was extracted twice with dichloromethane (50 mL)
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (ethyl acetate:methanol:triethylamine=10:1:0→10:1:0.5)

Quellen und Nachweise

ORD-Eintrag
ord-313e6e3a2c3b4af79543d3bb44c013f8
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822459B2

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