Reaktion #50749

Reaktionsgleichung

3-Phenyl-1H-pyrazolo[4,3-c]pyridine

ether

dimethylaminopropyl chloride

dimethylaminopropyl chloride

NaH

→

hydrochloride

1-[3-(Dimethylamino)propyl]-3-phenyl-1H-pyrazolo-[4,3-c]pyridine dihydrochloride

Lösungsmittel

dimethylformamide

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued for 1 hour
3. 3
   TemperaturAt the end of this time the reaction was warmed to 55° and, after an additional 2 hours
4. 4
   TemperaturWarming
5. 5
   workup.STIRRINGstirring
6. 6
   workup.WAITwas continued for 1 hour
7. 7
   SonstigeThe organic phase was dried
8. 8
   Sonstigeevaporated
9. 9
   Sonstigepurified by flash chromatography (5% triethylamine-ethyl acetate)
10. 10
    Sonstigegiving an oil
11. 11
    Sonstigeupon evaporation of the product-containing fractions

Vorschrift

3-Phenyl-1H-pyrazolo[4,3-c]pyridine (3.90 g) was suspended in 50 ml of dimethylformamide and 60% NaH (1.0 g) was added. After stirring for 90 minutes, dimethylaminopropyl chloride (3.0 g) was added, and stirring was continued for 1 hour. At the end of this time the reaction was warmed to 55° and, after an additional 2 hours, an additional 0.50 g of dimethylaminopropyl chloride was added. Warming and stirring was continued for 1 hour, after which time the reaction mixture was distributed between ether and H2O. The organic phase was dried, evaporated, and purified by flash chromatography (5% triethylamine-ethyl acetate), giving an oil upon evaporation of the product-containing fractions. The hydrochloride was formed in ethereal HCl and recrystallized from methanol-ether to give 3.76 g of product, m.p. 237°-239°.

Quelle