Ammonium Chloride → HCID 14181392, Verbindung

HRID 2231819

Reaktionsgleichung

Reaktionsgleichung von HRID 2231819
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH3:7].[Mg].[CH3:9][C:10]1([CH3:24])[CH2:23][N:14]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[C:21](=[O:22])[C:13]2=[N:12][CH2:11]1.[Cl-].[NH4+]>C(OCC)C.ClCCCl>[CH3:9][C:10]1([CH3:24])[CH2:23][N:14]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[C:21]([OH:22])([CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH3:7])[C:13]2=[N:12][CH2:11]1

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 5211681-Bromo-4-methoxybutaneHCID 5462224MagnesiumHCID 157447573,4-dihydro-3,3-dimethylpyrimido[1,2-a]indole-10(2H)-one

Produkt 1

HCID 14181392HCID 14181392, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of 1-bromo-4-methoxybutane (6.26 g) in diethyl ether (23 ml) was added dropwise to stirred magnesium turnings (0.9 g) under nitrogen, at a rate sufficient to maintain reflux. The mixture was stirred for a further 45 min., then a solution of 3,4-dihydro-3,3-dimethylpyrimido[1,2-a]indole-10(2H)-one (1.6 g) in 1,2-dichloroethane (75 ml) was added dropwise. The mixture was stirred for 30 min., then poured into aqueous ammonium chloride solution and extracted with chloroform (2×100 ml). The chloroform extracts were combined, dried (MgSO4) and evaporated under reduced pressure giving an orange solid. Trituration from ethyl acetate, followed by recrystallisation from ethyl acetate gave the title compound (1.2 g(. Addition of ethereal hydrogen chloride to a solution of the free base in methanol, followed by evaporation of the solvents and crystallisation of the resulting solid from propan-2-ol gave the hydrochloride salt (0.6 g), m.p. 188°-190°.

Aufarbeitung

  1. temperatureat a rate sufficient to maintain
  2. temperaturereflux
  3. stirringThe mixture was stirred for 30 min.
  4. extractionextracted with chloroform (2×100 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure
  7. customgiving an orange solid
  8. customTrituration from ethyl acetate, followed by recrystallisation from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-93010ce2609f400aab113940f6ed984a
Quelldatensatz
uspto-grants-1988_11
Patentnummer
US04784996

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