Water → 1-(5-Bromo-3,4-dihydroisoquinolin-2(1H)-yl)propan-2-one

HRID 1505043

Reaktionsgleichung

Reaktionsgleichung von HRID 1505043
Cl.[Br:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][NH:7][CH2:8]2.Cl[CH2:14][C:15](=[O:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[Br:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][N:7]([CH2:14][C:15](=[O:17])[CH3:16])[CH2:8]2

Komponenten

7

Edukt 4

HCID 962WaterHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 450740035-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride

Produkt 1

HCID 583180431-(5-Bromo-3,4-dihydroisoquinolin-2(1H)-yl)propan-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture containing 5-bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride (1 g, 4 mmol), chloroacetone (407 mg, 4.4 mmol) and potassium carbonate (1.38 g, 10 mmol) in dimethyl formamide (DMF) (8 ml) is stirred at room temperature for 18 hours. To this mixture is added water (50 ml) and ethyl acetate (50 ml). The organic layer is separated, washed with brine, dried over MgSO4, and concentrated. The crude product is purified by flash column chromatography using 30% ethyl acetate in dichloromethane as eluent to give 1-(5-Bromo-3,4-dihydroisoquinolin-2(1H)-yl)propan-2-one as an orange oil. LC-MS m/z: 269.1 (M+1).

Aufarbeitung

  1. customThe organic layer is separated
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product is purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fa029e8b621649dc8a8aca503df3aa64
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216964B2

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