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Water → (E)-1-(2-chloro-alpha-methoxycarbonylbenzyl)-3-(N,N-dimethylcarbamoyl)methylidene-4-hydroxypiperidine

HRID 397610
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 397610
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:12][N:13]([CH3:24])[C:14](/[CH:16]=[C:17]1\[CH2:18][NH:19][CH2:20][CH2:21][CH:22]\1[OH:23])=[O:15].[Cl:25][C:26]1[CH:37]=[CH:36][CH:35]=[CH:34][C:27]=1[CH:28](Br)[C:29]([O:31][CH3:32])=[O:30].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:25][C:26]1[CH:37]=[CH:36][CH:35]=[CH:34][C:27]=1[CH:28]([N:19]1[CH2:20][CH2:21][CH:22]([OH:23])/[C:17](=[CH:16]/[C:14](=[O:15])[N:13]([CH3:12])[CH3:24])/[CH2:18]1)[C:29]([O:31][CH3:32])=[O:30]
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Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 10730282Methyl alpha-bromo-2-chlorophenylacetateHCID 23000841(E)-3-(N,N-dimethylcarbamoyl)methylidene-4-hydroxypiperidine p-toluenesulfonate

Produkt 1

HCID 23000852(E)-1-(2-chloro-alpha-methoxycarbonylbenzyl)-3-(N,N-dimethylcarbamoyl)methylidene-4-hydroxypiperidineAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

7.95 g (23.3 mmol) of the (E)-3-(N,N-dimethylcarbamoyl)methylidene-4-hydroxypiperidine p-toluenesulfonate were dissolved in 50 ml of N,N-dimethylformamide (DMF), followed by the addition of 7.35 g (purity: 80.0%, 22.3 mmol) of 2-chloro-α-methoxycarbonylbenzyl bromide and 7.40 g (53.5 mmol) of potassium carbonate. The resulting mixture was stirred at room temperature for 15 hours. After completion of the reaction, 150 ml water were added. The resulting mixture was extracted with toluene and ethyl acetate. The extract was distilled under reduced pressure. The residue was then purified by chromatography on a silica gel column (eluting solvent: chloroform/methanol=9/1 to 4/1), whereby 6.38 g (77.9%) of the title compound were obtained as a yellowish brown oil.

Aufarbeitung

  1. additionwere added
  2. extractionThe resulting mixture was extracted with toluene and ethyl acetate
  3. distillationThe extract was distilled under reduced pressure
  4. customThe residue was then purified by chromatography on a silica gel column (eluting solvent: chloroform/methanol=9/1 to 4/1)

Quellen und Nachweise

ORD-Eintrag
ord-afd36c520715487ea08bbc7da419b298
Quelldatensatz
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06610708B1

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