Acetic Acid → 5-(4-Chlorophenyl)-2-(1-methylpiperidin-4-yl)pyrimidine

HRID 393742Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 393742
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([C:14]3[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH:19]=3)=[N:12][CH:13]=2)=[CH:4][CH:3]=1.CO.C(O)(=O)C>C(OCC)(=O)C.[Pt](=O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([CH:14]3[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]3)=[N:12][CH:13]=2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 887MethanolHCID 226466955-(4-Chlorophenyl)-2-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)pyrimidine

Produkt 1

HCID 226466965-(4-Chlorophenyl)-2-(1-methylpiperidin-4-yl)pyrimidineAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 345198Adams' catalystKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Platinum(IV) oxide (30 mg) was added to a solution of 5-(4-chlorophenyl)-2-(1-methyl-1,2,3,6-tetrahydropyridin -4-yl)pyrimidine (0.31 g) in a mixture of ethyl acetate (20 ml), methanol (3 ml) and acetic acid (1 ml) and the mixture was hydrogenated at atmospheric pressure for 18 h. The mixture was then filtered through celite, washing with 10% methanol/ethyl acetate, and evaporated under reduced pressure. The residue was treated with 2 M sodium hydroxide (15 ml) and extracted with diethyl ether (2×25 ml), and the organic extracts were washed with water (2×10 ml), saturated brine (20 ml), dried (Na2SO4) and evaporated under reduced pressure and the residue purified by silica gel column chromatography with 10% methanol/dichloromethane with 0.5% concentrated aqueous ammonia as eluent, to yield the title compound as a white solid (0.14 g, 45%).

Aufarbeitung

  1. filtrationThe mixture was then filtered through celite
  2. washwashing with 10% methanol/ethyl acetate
  3. customevaporated under reduced pressure
  4. additionThe residue was treated with 2 M sodium hydroxide (15 ml)
  5. extractionextracted with diethyl ether (2×25 ml)
  6. washthe organic extracts were washed with water (2×10 ml), saturated brine (20 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated under reduced pressure
  9. customthe residue purified by silica gel column chromatography with 10% methanol/dichloromethane with 0.5% concentrated aqueous ammonia as eluent

Quellen und Nachweise

ORD-Eintrag
ord-ceb51a803c5445b7ae77ac2c5c6d8e76
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809100B2

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