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Benzyl chloroformate → HCID 67366402, Verbindung

HRID 2387944
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2387944
[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 equiv.) of Cbz chloride were added dropwise, over a period of 1 hour, to 50 g (1 equiv.) of 1-benzyl-N,N-dimethyl-4-phenylpiperidine-4-amine, and the resulting reaction mixture was stirred for 2 hours at room temperature. The progress of the reaction was monitored by thin-layer chromatography (10% MeOH/CHCl3). When the reaction was complete, the mixture was cooled to 0° C. and rendered basic with saturated sodium hydrogen carbonate solution, and the reaction mixture was extracted 3× with 300 ml of EtOAc. The combined organic phases were dried with Na2SO4. After removal of the solvent under reduced pressure, purification was carried out by column chromatography (silica gel; 50% EtOAc/heptane). 12 g (21%) of product were obtained in the form of an oil.

Aufarbeitung

  1. customthe resulting reaction mixture
  2. temperaturethe mixture was cooled to 0° C.
  3. extractionthe reaction mixture was extracted 3× with 300 ml of EtOAc
  4. dry with materialThe combined organic phases were dried with Na2SO4
  5. customAfter removal of the solvent
  6. customunder reduced pressure, purification

Quellen und Nachweise

ORD-Eintrag
ord-67d0c36e8bd345ce81afdae822e1aa93
Quelldatensatz
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08269000B2

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