Pyridine → 2-methyl-4-phenoxy-1-[2-(3-pyridin-3-ylpropoxy)ethyl]-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinoline

HRID 432711Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432711
[O:1]([C:8]1[C:17]([NH2:18])=[C:16]([NH:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=[CH:34][CH:33]=1.C(Cl)(=O)C>C(OCC)(=O)C>[CH3:33][C:34]1[N:19]([CH2:20][CH2:21][O:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[C:16]2[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[N:9]=[C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:17]=2[N:18]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 187601982-phenoxy-N4-[2-(3-pyridin-3-ylpropoxy)ethyl]-5,6,7,8-tetrahydroquinoline-3,4-diamine

Produkt 1

HCID 187602012-methyl-4-phenoxy-1-[2-(3-pyridin-3-ylpropoxy)ethyl]-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolineAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A 200 ml round bottom flask was charged with 2-phenoxy-N4-[2-(3-pyridin-3-ylpropoxy)ethyl]-5,6,7,8-tetrahydroquinoline-3,4-diamine (4.1 g, 0.0098 mol.) and pyridine (40 mL) at room temperature. To this solution was slowly added acetyl chloride (0.8 g, 0.011 mol., 1.1 equivalents). The reaction was maintained with stirring at room temperature. After two hours the reaction was monitored and found to only contain the amide intermediate. The reaction mixture was then heated to reflux and maintained overnight. The reaction mixture was concentrated to provide a dark amber syrup. The syrup was taken up in ethyl acetate (300 mL) and washed with water (2×100 mL). The ethyl acetate layer was concentrated to provide 2-methyl-4-phenoxy-1-[2-(3-pyridin-3-ylpropoxy)ethyl]-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinoline as an orange syrup (3.8 g, 88%). TLC (10%MeOH/CH2Cl2, Rf=0.34). Mass-spec M+1=443.2

Aufarbeitung

  1. temperatureThe reaction was maintained
  2. temperatureThe reaction mixture was then heated
  3. temperatureto reflux
  4. temperaturemaintained overnight
  5. concentrationThe reaction mixture was concentrated
  6. customto provide a dark amber syrup
  7. washwashed with water (2×100 mL)
  8. concentrationThe ethyl acetate layer was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-74255c444eb14da89bbd11e935877874
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06664260B2

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