4-Chloropyridine → tert-Butyl [1-(pyridin-4-yl)piperidin-4-yl]carbamate

HRID 33241

Reaktionsgleichung

Reaktionsgleichung von HRID 33241
[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Cl[C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1>C(O)CCC.O.CCN(CC)CC.C(Cl)Cl>[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 122884-ChloropyridineHCID 7238334-(N-Boc-amino)piperidine

Produkt 1

HCID 18008972tert-Butyl [1-(pyridin-4-yl)piperidin-4-yl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 86625244n-butanol water NEt3Lösungsmittel

Versuchsvorschrift

A solution of 3 g Piperidin-4-yl-carbamic acid tert-butyl ester and 2.5 g 4-Chloropyridine in 9 ml n-butanol/water/NEt3 1:1:1 was heated at 100° C. for 48 h. Then the solution was cooled to RT diluted with DCM and washed with NaHCO3 solution and water. The organic layer was dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Chromatographic purification of the residue on silica with DCM as eluent gave after evaporation of the fractions containing the product a white foam. Yield 1.7 g.

Aufarbeitung

  1. washwashed with NaHCO3 solution and water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customChromatographic purification of the residue on silica with DCM as eluent
  6. customgave
  7. customafter evaporation of the fractions
  8. additioncontaining the product a white foam

Quellen und Nachweise

ORD-Eintrag
ord-67cb0225ae7f4dc89bfb109598d6f565
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429581B2

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