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Dimethylamine → HCID 21939837, Verbindung

HRID 1242928
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1242928
CS(Cl)(=O)=O.O[CH2:7][CH2:8][C:9]1[CH2:18][CH2:17][C:16]2[CH:15]=[C:14]([NH:19][C:20](=[O:22])[CH3:21])[CH:13]=[CH:12][C:11]=2[CH:10]=1.[CH2:23]([N:25](CC)[CH2:26]C)C.CNC>O1CCCC1.CN(C)C=O>[CH3:23][N:25]([CH3:26])[CH2:7][CH2:8][C:9]1[CH2:18][CH2:17][C:16]2[CH:15]=[C:14]([NH:19][C:20](=[O:22])[CH3:21])[CH:13]=[CH:12][C:11]=2[CH:10]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21939867HCID 21939867, Verbindung

Produkt 1

HCID 21939837HCID 21939837, VerbindungAusbeute 52,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228
Dimethylformamide
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methanesulfonyl chloride (0.0393 ml, 0.469 mmol) was added to a dimethylformamide solution (2 ml) of N-[6-(2-hydroxyethyl)-7,8-dihydro-2-naphthalenyl]acetamide (102 mg, 0.426 mmol) obtained in Reference Example 102 and triethylamine (0.0652 ml, 0.469 mmol) under ice-cooling, which was stirred for 30 minutes. A tetrahydrofuran solution (0.64 ml) of 2N dimethylamine was added to the reaction mixture, which was stirred at 60° C. for 5 hours. The solvent was distilled out under reduced pressure. Ethyl acetate was added to the residue, and extraction was conducted using 1N hydrochloric acid. Potassium carbonate was added to the extract to make it alkaline, and extraction was conducted using ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was distilled out under reduced pressure. The resulting residue was purified by alumina column chromatography (development solvent; ethyl acetate), to give the titled compound (57.5 mg).

Aufarbeitung

  1. temperaturecooling
  2. stirringwas stirred at 60° C. for 5 hours
  3. distillationThe solvent was distilled out under reduced pressure
  4. additionEthyl acetate was added to the residue, and extraction
  5. additionPotassium carbonate was added to the
  6. extractionextract
  7. extractionextraction
  8. washThe extract was washed with saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationthe solvent was distilled out under reduced pressure
  11. customThe resulting residue was purified by alumina column chromatography (development solvent; ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-aefb2dc349c147c997b4c27411343578
Quelldatensatz
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07115750B1

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