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Potassium Carbonate → (E)-N-[4-[N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylaminomethyl]phenyl]-3-(4-methylphenyl)cinnamamide hydrochloride

HRID 1277080
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1277080
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:26])/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[CH:14]=2)=[CH:5][CH:4]=1.[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH2:37][CH2:38][NH:39][CH3:40])[CH:32]=[CH:33][C:34]=1[O:35][CH3:36].C(=O)([O-])[O-].[K+].[K+].C(OC(=O)C)C.Cl>CN(C=O)C.C(OCC)(=O)C.O>[ClH:1].[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH2:37][CH2:38][N:39]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:26])/[CH:11]=[CH:12]/[C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]4[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=4)[CH:14]=3)=[CH:5][CH:4]=2)[CH3:40])[CH:32]=[CH:33][C:34]=1[O:35][CH3:36]
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Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 77039N-MethylhomoveratrylamineHCID 18472214(E)-N-[4-(chloromethyl)phenyl]3-(4-methylphenyl)cinnamamideHCID 21866389Hydrogen chloride-ethyl acetate

Produkt 1

HCID 18472486(E)-N-[4-[N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylaminomethyl]phenyl]-3-(4-methylphenyl)cinnamamide hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In DMF (3 ml) was dissolved (E)-N-[4-(chloromethyl)phenyl]-3- (4-methylphenyl)cinnamamide (200 mg), and to the solution were added 2-(3,4-dimethoxyphenyl)ethylmethylamine (132 μl) and potassium carbonate (382 mg). The mixture was stirred at room temperature for 12 hours, and to the mixture was added water (50 ml). The mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate) to give colorless amorphous, which was dissolved in ethyl acetate (50 ml), and to the mixture was added 4N hydrochloric acid ethyl acetate solution (0.5 ml). The resulting precipitate was filtered and recrystallized from ethyl acetate-methanol to give (E)-N-[4-[N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylaminomethyl]phenyl]-3-(4-methylphenyl)cinnamamide hydrochloride (Compound 63) (245 mg) as colorless crystals.

Aufarbeitung

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified with column chromatography (ethyl acetate)
  7. customto give colorless amorphous, which
  8. filtrationThe resulting precipitate was filtered
  9. customrecrystallized from ethyl acetate-methanol

Quellen und Nachweise

ORD-Eintrag
ord-db1d224bdb9745c588012b68b422b9b8
Quelldatensatz
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06166006

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