Dimethylamine, hydrochloride → N,N-Dimethyl-2-oxo-1,2,3,4-tetrahydro-3-quinolineacetoamide

HRID 2269713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2269713
[O:1]=[C:2]1[CH:11]([CH2:12][C:13]([OH:15])=O)[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.C[CH2:17][N:18]=[C:19]=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.CNC>C1COCC1.C(#N)C.O.C(N(CC)CC)C>[CH3:17][N:18]([CH3:19])[C:13](=[O:15])[CH2:12][CH:11]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2]1=[O:1]

Komponenten

9

Edukt 4

HCID 10473Dimethylamine, hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 183329702-(2-Oxo-1,2,3,4-tetrahydroquinolin-3-YL)acetic acid

Produkt 1

HCID 10585665N,N-Dimethyl-2-oxo-1,2,3,4-tetrahydro-3-quinolineacetoamideAusbeute 67,6 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To the mixed solution of 2-oxo-1,2,3,4-tetrahydro-3-quinolineacetic acid (810 mg) in THF (10 ml) and acetonitrile (10 ml), WSC (1.15 g), HOBt (610 mg), dimethylamine hydrochloride (650 mg) and triethylamine (1.67 ml) were added subsequently, which was stirred at room temperature overnight. Water was added to the reaction mixture, which was extracted with a mixed solvent of ethyl acetate-THF (1:1). The organic layer was washed subsequently with 0.1N aqueous hydrochloric acid solution, a saturated aqueous sodium bicarbonate solution, and a saturated aqueous sodium chloride solution, then dried and concentrated to obtain the entitled compound (620 mg).

Aufarbeitung

  1. extractionwas extracted with a mixed solvent of ethyl acetate-THF (1:1)
  2. washThe organic layer was washed subsequently with 0.1N aqueous hydrochloric acid solution
  3. dry with materiala saturated aqueous sodium bicarbonate solution, and a saturated aqueous sodium chloride solution, then dried
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-da3c7ded1c084ffcaa59d359b91b513d
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06329389B1

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