Реакция #42383

Уравнение реакции

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

triethylamine

bromobutane

→

title compound

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

Растворители

methylene chloride

methylene chloride

Условия реакции

Обработка

1. 1
   Промывкаwashed with water, and brine
2. 2
   Сушкаdried (magnesium sulfate)
3. 3
   Фильтрацияfiltered
4. 4
   Концентрированиеconcentrated under reduced pressure
5. 5
   ДругоеPurification by flash column chromatography (silica, 50% ethyl acetate/hexanes)

Методика

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]+.

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