Reaktion #42383

Reaktionsgleichung

1,2,3,4-tetrahydroisoquinoline-7-carbonitrile

triethylamine

bromobutane

→

title compound

2-Butyl-1,2,3,4-tetrahydroisoquinoline-7-carbonitrile

Lösungsmittel

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with water, and brine
2. 2
   Trocknendried (magnesium sulfate)
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   SonstigePurification by flash column chromatography (silica, 50% ethyl acetate/hexanes)

Vorschrift

To an ice-cold, stirred solution of 1,2,3,4-tetrahydroisoquinoline-7-carbonitrile (J. Med. Chem. 1997, 40, 3997) (485 mg, 3.1 mmol) and triethylamine (0.47 mL, 3.4 mmol) in methylene chloride (5 mL) is added DMAP (37 mg, 0.3 mmol) and bromobutane (0.5 mL, 4.6 mmol). The reaction mixture is stirred for 20 h, diluted with methylene chloride, washed with water, and brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 50% ethyl acetate/hexanes) affords the title compound. ESI MS m/z 215 [M+H]+.

Quelle