Reacción #42383

Ecuación de reacción

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

triethylamine

bromobutane

→

title compound

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

Disolventes

methylene chloride

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with water, and brine
2. 2
   Secadodried (magnesium sulfate)
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated under reduced pressure
5. 5
   OtroPurification by flash column chromatography (silica, 50% ethyl acetate/hexanes)

Procedimiento

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]+.

Fuente