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4-Chloropyridine → tert-Butyl methyl((1-(pyrimidin-4-yl)piperidin-4-yl)methyl)carbamate

HRID 1193344
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1193344
[CH3:1][N:2]([CH2:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].Cl[C:18]1[CH:23]=[CH:22][N:21]=[CH:20]C=1.CC[N:26](C(C)C)C(C)C>CC(O)C.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[CH3:1][N:2]([CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][N:26]=2)[CH2:13][CH2:12]1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:6])[CH3:7]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 122884-ChloropyridineHCID 81531DiisopropylethylamineHCID 23004743tert-butyl N-methyl-N-(piperidin-4-ylmethyl)carbamate

Produkt 1

HCID 66805336tert-Butyl methyl((1-(pyrimidin-4-yl)piperidin-4-yl)methyl)carbamateAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3776IsopropanolLösungsmittel
HCID 8857
Ethyl Acetate
Lösungsmittel
HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

tert-Butyl methyl(piperidin-4-ylmethyl)carbamate (1.4 mmol, 1.0 eq) and 4-chloropyridine (4.2 mmol, 3.0 eq) were dissolved in 2-propanol (5 ml) and DIPEA (7.0 mmol. 5.0 eq) and refluxed for 16 hours. After monitoring by TLC, the reaction solution was diluted with ethyl acetate and sat. sodium hydrogen carbonate solution and the phases were separated. The aqueous phase was washed with ethyl acetate. The combined organic phases were dried over magnesium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, ethyl acetate:ethanol 10:1+ammonia solution). Yield: 51%

Aufarbeitung

  1. customthe phases were separated
  2. washThe aqueous phase was washed with ethyl acetate
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. custompurified by column chromatography (silica gel, ethyl acetate:ethanol 10:1+ammonia solution)

Quellen und Nachweise

ORD-Eintrag
ord-bb171c432a9b41bb922c24e5ec84f199
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08680159B2

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