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Benzyl chloroformate → HCID 67366402, Verbindung

HRID 453880
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 453880
[C:1](Cl)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C([N:19]1[CH2:24][CH2:23][C:22]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([N:25]([CH3:27])[CH3:26])[CH2:21][CH2:20]1)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>CO.C(Cl)(Cl)Cl>[CH2:4]([O:3][C:1]([N:19]1[CH2:24][CH2:23][C:22]([N:25]([CH3:27])[CH3:26])([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:21][CH2:20]1)=[O:2])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1
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Komponenten

5

Edukt 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 68409296HCID 68409296, Verbindung

Produkt 1

HCID 67366402HCID 67366402, VerbindungAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584188Chloroform methanolLösungsmittel

Versuchsvorschrift

500 ml (10 eq.) Cbz chloride were added dropwise to 50 g (1 eq.) 1-benzyl-N,N-dimethyl-4-phenylpiperidin-4-amine over a period of 1 h and the reaction mixture obtained was stirred for 2 h at room temperature. The reaction course was monitored by thin-layer chromatography (10% MeOH/CHCl3). Once the conversion was complete, the reaction mixture was cooled to 0° C., made alkaline with saturated sodium hydrogen carbonate solution and extracted 3 times with 300 ml EtOAc. The combined organic phases were dried with Na2SO4. Following removal of the solvent under reduced pressure, the residue was purified by column chromatography (silica gel; 50% EtOAc/heptane). 12 g (21%) of product were obtained in the form of an oil.

Aufarbeitung

  1. customthe reaction mixture obtained
  2. temperaturethe reaction mixture was cooled to 0° C.
  3. extractionextracted 3 times with 300 ml EtOAc
  4. dry with materialThe combined organic phases were dried with Na2SO4
  5. customremoval of the solvent under reduced pressure
  6. customthe residue was purified by column chromatography (silica gel; 50% EtOAc/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-d1540ac7271e48589aa9094a04993786
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08492559B2

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