Hydrochloric Acid → HCID 14022356, Verbindung

HRID 1732329Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1732329
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([Cl:16])[N:3]=1.[CH2:17]([O:19][CH2:20][CH2:21][O:22][CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[CH3:18].C(N(CC)CC)C.Cl>C(O)CCC.C(O)C>[ClH:16].[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:26]2[CH2:27][CH2:28][CH:23]([O:22][CH2:21][CH2:20][O:19][CH2:17][CH3:18])[CH2:24][CH2:25]2)[N:3]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 140223854-(2-Ethoxyethoxy)piperidine

Produkt 1

HCID 14022356HCID 14022356, VerbindungAusbeute 45,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2631-ButanolLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

4-Amino-2-chloro-6,7-dimethoxyquinazoline (4.3 g.), 4-(2-ethoxyethoxy)piperidine (3.2 g.) and triethylamine (10 ml.) in n-butanol (400 ml.) were heated at reflux overnight under an atmosphere of nitrogen. The mixture was then cooled, evaporated in vacuo, and the residue basified (aqueous Na2CO3) and extracted 3 times with chloroform. The combined chloroform extracts were evaporated and the residue chromatographed on neutral alumina (150 g., Grade I, deactivated with 5 ml water). Elution with chloroform gave the crude product (3.6 g.) which was converted to the hydrochloride salt by treatment with hydrogen chloride in ethanol. The hydrochloride was then recrystallized from ethanol/isopropanol to give 4-amino-6,7-dimethoxy-2-[4-(2-ethoxyethoxy)piperidino]quinazoline hydrochloride (3.4 g.), m.p. 219°-220° C.

Aufarbeitung

  1. temperatureat reflux overnight under an atmosphere of nitrogen
  2. temperatureThe mixture was then cooled
  3. customevaporated in vacuo
  4. extractionextracted 3 times with chloroform
  5. customThe combined chloroform extracts were evaporated
  6. customthe residue chromatographed on neutral alumina (150 g., Grade I, deactivated with 5 ml water)
  7. washElution with chloroform
  8. customgave the crude product (3.6 g.) which
  9. customThe hydrochloride was then recrystallized from ethanol/isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-51b1d4af8f95421ea7e034b6a543f1b8
Quelldatensatz
uspto-grants-1980_12
Patentnummer
US04237138

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