Réaction #42383

Équation de réaction

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

triethylamine

bromobutane

→

title compound

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

Solvants

methylene chloride

methylene chloride

Conditions de réaction

Traitement

1. 1
   Lavagewashed with water, and brine
2. 2
   Séchagedried (magnesium sulfate)
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   AutrePurification by flash column chromatography (silica, 50% ethyl acetate/hexanes)

Mode opératoire

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]+.

Source