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

HRID 432711노트

반응식

HRID 432711 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-74255c444eb14da89bbd11e935877874
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06664260B2

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