Reaktion #55528

Reaktionsgleichung

sodium hydride

sodium borohydride

methyl iodide

2-(1-pyrrolidinyl)-2-(2-pyridyl)acetonitrile

pyridine-2-carboxaldehyde

potassium cyanide

pyrrolidinium perchlorate

→

1-(1-pyrrolidinyl)-1-(2-pyridyl)ethane

Ausbeute 88.0%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

ethanol

dimethylsulfoxide

hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter addition
2. 2
   Temperaturthe reaction mixture was warmed to 40° for two minutes
3. 3
   Temperaturcooled to 15°
4. 4
   FiltrationThe reaction mixture was filtered
5. 5
   Waschenthe precipitate was washed with methylene chloride
6. 6
   Waschenwashed with saturated sodium chloride solution
7. 7
   Trocknendried over sodium sulfate
8. 8
   SonstigeRemoval of the solvent
9. 9
   Sonstigegave 24.75 g (92%) of the crude product, 2-(1-pyrrolidinyl)-2-(2-pyridyl)propionitrile
10. 10
    Temperaturcooled to 5°
11. 11
    Filtrationfiltered
12. 12
    SonstigeRemoval of the solvent at reduced pressure
13. 13
    Sonstigegave a tan oil which
14. 14
    Trocknendried over sodium sulfate
15. 15
    FiltrationThe hexane solution was then filtered
16. 16
    Einengenconcentrated
17. 17
    workup.DISTILLATIONThe crude product was distilled (78°-80°/0.2 mm Hg)

Vorschrift

To 25.0 g (0.134 mol) of 2-(1-pyrrolidinyl)-2-(2-pyridyl)acetonitrile, prepared by the reaction of pyridine-2-carboxaldehyde with potassium cyanide and pyrrolidinium perchlorate, in 75 ml dry dimethylsulfoxide and 200 ml tetrahydrofuran at -10° was added 7.75 g (0.161 mol) of 50% sodium hydride dispersion. After no further gas evolution was observed, a solution of 22.34 g (0.161 mol) of methyl iodide in 10 ml tetrahydrofuran was added over a 10 minute period. After addition had been completed, the reaction mixture was warmed to 40° for two minutes and cooled to 15°. The reaction mixture was filtered and the precipitate was washed with methylene chloride. The filtrates were combined, washed with saturated sodium chloride solution, and dried over sodium sulfate. Removal of the solvent gave 24.75 g (92%) of the crude product, 2-(1-pyrrolidinyl)-2-(2-pyridyl)propionitrile. The total crude product was dissolved in 500 ml 95% ethanol, cooled to 5° and treated with 9.3 g (0.245 mol) sodium borohydride. The reaction mixture was stirred at room temperature for 20 hours and then filtered. Removal of the solvent at reduced pressure gave a tan oil which was dissolved in hexane and dried over sodium sulfate. The hexane solution was then filtered and concentrated. The crude product was distilled (78°-80°/0.2 mm Hg) to give 20.77 g (88%) of 1-(1-pyrrolidinyl)-1-(2-pyridyl)ethane.

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