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Hydrochloric Acid → N-(1H-indol-1-yl)-N-propyl-9H-purin-6-amine

HRID 465968
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 465968
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.Cl.[N:12]1([NH:21][CH2:22][CH2:23][CH3:24])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13]1.C([O-])([O-])=O.[Na+].[Na+]>CN1CCCC1=O.O>[N:12]1([N:21]([CH2:22][CH2:23][CH3:24])[C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][NH:6]3)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 53592776-ChloropurineHCID 107023901H-Indol-1-amine, N-propyl-

Produkt 1

HCID 178456864N-(1H-indol-1-yl)-N-propyl-9H-purin-6-amineAusbeute 25,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 13387N-methyl-2-pyrrolidoneLösungsmittel2×

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 6-chloropurine (5.0 g, 0.032 mole) in 50 ml 1-methyl-2-pyrrolidinone, was added 1 ml ethereal-HCl; followed by a solution of N-(1H-indol-1-yl)-N-propylamine (5.2 g, 0.030 mole) in 50 ml 1-methyl-2-pyrrolidinone. After stirring at 120° C. for six hours, the mixture was cooled, poured into 500 ml water and stirred for five minutes, pH adjusted to 10 with Na2CO3 ; then extracted with ethyl acetate. The organic layer was washed with water, then dried (saturated NaCl, anhydrous MgSO4). After filtering, the solution was evaporated to an oil, about 8 g, which was eluted on a silica gel column with ethyl acetate via high pressure liquid chromatography. The desired fractions were combined, then evaporated to yield 2.2 g (25%) of N-(1H-indol-1-yl)-N-propyl-9H-purin-6-amine, m.p. 90°-5° C.

Aufarbeitung

  1. temperaturethe mixture was cooled
  2. stirringstirred for five minutes
  3. extractionthen extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried (saturated NaCl, anhydrous MgSO4)
  6. filtrationAfter filtering
  7. customthe solution was evaporated to an oil, about 8 g, which
  8. washwas eluted on a silica gel column with ethyl acetate via high pressure liquid chromatography
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-5e21a73129ce470a9cdb6208078de0f6
Quelldatensatz
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05155098

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