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

HRID 22471

Reaktionsgleichung

Reaktionsgleichung von HRID 22471
[C:1]1([C:7]2[C:11]3[CH:12]=[N:13][CH:14]=[CH:15][C:10]=3[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:18][N:19]([CH2:21][CH2:22][CH2:23][Cl:24])[CH3:20].CCOCC>CN(C)C=O.O>[ClH:24].[ClH:24].[CH3:18][N:19]([CH3:20])[CH2:21][CH2:22][CH2:23][N:9]1[C:10]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8]1

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamine2×HCID 138011253-Phenyl-1H-pyrazolo[4,3-c]pyridine

Produkt 1

HCID 199304801-[3-(Dimethylamino)propyl]-3-phenyl-1H-pyrazolo[4,3-c]pyridine dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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°.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 1 hour
  3. temperatureAt the end of this time the reaction was warmed to 55° and, after an additional 2 hours
  4. temperatureWarming
  5. stirringstirring
  6. waitwas continued for 1 hour
  7. customThe organic phase was dried
  8. customevaporated
  9. custompurified by flash chromatography (5% triethylamine-ethyl acetate)
  10. customgiving an oil
  11. customupon evaporation of the product-containing fractions

Quellen und Nachweise

ORD-Eintrag
ord-4913146aa9ce408792d93d92a3809610
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428169

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