Sodium Hydroxide → HCID 21487853, Verbindung

HRID 1414574Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1414574
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[N:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1.[NH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1.[BH4-].[Na+].[OH-].[Na+]>C1C=CC=CC=1.CCOCC.O.C(O)(=O)C.C(O)C>[N:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][NH:22][CH:18]1[CH2:19][CH2:20][N:15]([C:6]2[C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=[CH:8][N:7]=2)[CH2:16][CH2:17]1

Komponenten

10

Edukt 4

HCID 14798Sodium HydroxideHCID 195092-PyridinemethanamineHCID 4311764Sodium borohydrideHCID 147388231-(6,7-Dimethoxy-4-quinazolinyl)-4-piperidinone

Produkt 1

HCID 21487853HCID 21487853, VerbindungAusbeute 52,2 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 176Acetic AcidLösungsmittelHCID 241BenzeneLösungsmittelHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

1-(6,7-Dimethoxyquinazolin-4-yl)piperid-4-one (2.9g) (which may be prepared as in part A of Example 91, hereinafter), and 2-aminomethylpyridine (1.19g) were refluxed together for two hours in benzene (50 ml.) in a flask fitted with a Dean and Stark trap. Ethanol (50 ml.) was added to the cooled solution followed by the slow addition of sodium borohydride (0.76g) with stirring. On completion of the addition stirring as continued for two hours followed by the addition of excess acetic acid. The mixture was poured into water, basified with 5N sodium hydroxide and was extracted with chloroform. Evaporation of the chloroform layer gave a yellow oil which solidified on trituration with ether. Recrystallization from ethyl acetate gave 4-[4-(2-pyridylmethyl-amino)piperidino]-6,7-dimethoxyquinazoline (2 g) m.p. 151°-155° C.

Aufarbeitung

  1. customfitted with a Dean and Stark trap
  2. additionOn completion of the addition
  3. stirringstirring
  4. extractionwas extracted with chloroform
  5. customEvaporation of the chloroform layer
  6. customgave a yellow oil which
  7. customRecrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ef547666bb804d20b90fd13fe304d326
Quelldatensatz
uspto-grants-1977_01
Patentnummer
US04001422

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