Triethylamine → 1-(6,7-Dimethoxy-4-quinazolinyl)-4-piperidinone

HRID 1414576Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1414576
Cl[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]=[CH:4][N:3]=1.Cl.C1O[C:20]2([CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[O:19]C1.C(N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+]>Cl.C(O)C>[O:19]=[C:20]1[CH2:25][CH2:24][N:23]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][N:3]=2)[CH2:22][CH2:21]1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 162187951,4-Dioxa-8-azaspiro(4.5)decane hydrochloride

Produkt 1

HCID 147388231-(6,7-Dimethoxy-4-quinazolinyl)-4-piperidinoneAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

4-Chloro-6,7-dimethoxyquinazoline (30 g), 4-piperidone ethylene ketal hydrochloride (25 g), triethylamine (35 g) and ethanol (250 ml.) were refluxed together for 3 hours. Aqueous sodium carbonate was added followed by extraction with chloroform after which the chloroform extract was dried and evaporated in vacuo to give an oil. The oil was redissolved in aqueous hydrochloric acid (1.5N, 200 ml.) and refluxed for 2 hours followed by cooling, basification (Na2CO3 10% soln) and extraction into chlororform. Evaporation of the dried chloroform extract gave 4-(4-oxo-piperidino)-6,7-dimethoxyquinazoline (37.6 g) m.p. 176°-8° C.

Aufarbeitung

  1. extractionfollowed by extraction with chloroform after which the chloroform
  2. extractionextract
  3. customwas dried
  4. customevaporated in vacuo
  5. customto give an oil
  6. temperaturerefluxed for 2 hours
  7. temperatureby cooling
  8. extractionbasification (Na2CO3 10% soln) and extraction into chlororform
  9. customEvaporation of the dried chloroform
  10. extractionextract

Quellen und Nachweise

ORD-Eintrag
ord-074f683bb77c4dde8950488fef0c78a2
Quelldatensatz
uspto-grants-1977_01
Patentnummer
US04001422

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