Reaktion #367419

Reaktionsgleichung

dimethylsulfide

borane dimethylsulfide

4-(3-chloropropyl)-2-cyanopyridine

→

2-aminomethyl-4-(3-chloropropyl)pyridine

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONsimultaneously distills off
2. 2
   TemperaturThe mixture is refluxed for 15 minutes
3. 3
   workup.ADDITIONafter the addition
4. 4
   Temperaturcooled to 30°
5. 5
   workup.ADDITION6 ml of 6N hydrochloric acid is added
6. 6
   TemperaturAfter hydrogen evolution ceases, the mixture is refluxed for 30 minutes
7. 7
   Temperaturcooled to 0° and saturated with solid sodium carbonate
8. 8
   Extraktionbefore extracting with methylene chloride (4×50 ml)
9. 9
   TrocknenThe organic extracts are dried over sodium sulfate
10. 10
    Sonstigeevaporated
11. 11
    Sonstigeto yield an oil which
12. 12
    Filtrationis filtered through 10 g of silica gel (1:1 EtOAc-MeOH)

Vorschrift

A solution of borane-dimethylsulfide (0.83 ml, 7.7 mmol) in 7 ml of tetrahydrofuran is added slowly to a refluxing solution of 4-(3-chloropropyl)-2-cyanopyridine (1.24 g, 6.9 mmol) in 7 ml of tetrahydrofuran while dimethylsulfide simultaneously distills off. The mixture is refluxed for 15 minutes after the addition is complete, cooled to 30° and 6 ml of 6N hydrochloric acid is added. After hydrogen evolution ceases, the mixture is refluxed for 30 minutes, cooled to 0° and saturated with solid sodium carbonate before extracting with methylene chloride (4×50 ml). The organic extracts are dried over sodium sulfate and evaporated to yield an oil which is filtered through 10 g of silica gel (1:1 EtOAc-MeOH) to yield 2-aminomethyl-4-(3-chloropropyl)pyridine as a yellow oil; NMR (CDCl3) 3.55 (t, 2H), 4.20 (s, 2H).

Quelle