Methanol → 5-(4-Chlorophenyl)-2-piperidin-4-ylpyrimidine

HRID 1005893Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1005893
ClC(OC(Cl)C)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[N:17][C:18]([CH:21]3[CH2:26][CH2:25][N:24](C)[CH2:23][CH2:22]3)=[N:19][CH:20]=2)=[CH:11][CH:10]=1.CO>ClCCCl.C(OCC)C>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[N:17][C:18]([CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)=[N:19][CH:20]=2)=[CH:11][CH:10]=1

Komponenten

6

Edukt 3

HCID 887MethanolHCID 5213051-Chloroethyl chloroformateHCID 226466965-(4-Chlorophenyl)-2-(1-methylpiperidin-4-yl)pyrimidine

Produkt 1

HCID 226466975-(4-Chlorophenyl)-2-piperidin-4-ylpyrimidineAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

1-Chloroethyl chloroformate (0.50 ml) was added to a solution of 5-(4-chlorophenyl)-2-(1-methylpiperidin-4-yl)pyrimidine (0.170 g) in anhydrous 1,2-dichloroethane (10 ml) and the mixture heated to reflux, under a calcium chloride guard tube, for 20 h. The reaction was then cooled, treated with methanol (1.0 ml), and returned to reflux for a further hour. After cooling, the reaction was diluted with diethyl ether (20 ml) and extracted with water (20 ml), 0.2 M hydrochloric acid (10 ml) then 1% citric acid (50 ml). The combined aqueous extracts were back-extracted with diethyl ether (10 ml), basified to pH 13 with 46% aqueous sodium hydroxide and extracted with ethyl acetate (20 ml, then 2×10 ml). The combined ethyl acetate extracts were washed with water (10 ml), saturated brine (20 ml), dried (Na2SO4) and evaporated under reduced pressure to give the title compound as a white solid (0.123 g, 76%).

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureto reflux, under a calcium chloride guard tube
  3. temperatureThe reaction was then cooled
  4. temperatureto reflux for a further hour
  5. temperatureAfter cooling
  6. extractionextracted with water (20 ml), 0.2 M hydrochloric acid (10 ml)
  7. extractionThe combined aqueous extracts were back-extracted with diethyl ether (10 ml)
  8. extractionextracted with ethyl acetate (20 ml
  9. washThe combined ethyl acetate extracts were washed with water (10 ml), saturated brine (20 ml)
  10. dry with materialdried (Na2SO4)
  11. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a942fe970b384fb3847d6885bce15860
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06787536B2

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