Hydrogen Peroxide → 4-{[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzaldehyde oxime

HRID 8950

Reaktionsgleichung

Reaktionsgleichung von HRID 8950
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]([CH:21]1[C:30]2[N:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH2:24][CH2:23][CH2:22]1)[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][NH2:20])=[CH:15][CH:14]=1.OO.C(=O)(O)[O-:34].[Na+]>CO.O.O.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]([CH:19]=[N:20][OH:34])=[CH:17][CH:18]=1)[CH:21]1[C:30]2[N:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH2:24][CH2:23][CH2:22]1

Komponenten

6

Edukt 3

HCID 784Hydrogen PeroxideHCID 516892Sodium BicarbonateHCID 21985008N-[(1H-Benzo[d]imidazol-2-yl)methyl]-N-(4-(aminomethyl)-benzyl)-5,6,7,8-tetrahydroquinolin-8-amine

Produkt 1

HCID 738578984-{[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzaldehyde oximeAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 150191Sodium Tungstate DihydrateKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (200 mg, 0.50 mmol) in MeOH (5 mL) was added solid sodium tungstate dihydrate (332 mg, 1.0 mmol) followed by a 35 wt % aqueous solution of hydrogen peroxide (2.9 mL, 30 mmol). The resulting suspension was stirred 3 h, then saturated aqueous sodium bicarbonate (5 mL) was added. The phases were separated and the aqueous layer was extracted with CH2Cl2 (3×10 mL), then the combined organic extracts were washed once with brine (10 mL), dried (MgSO4), and concentrated in vacuo. Purification of the crude material by flash chromatography (silica gel, 75:1:1 CH2Cl2MeOH/NH4OH) afforded the title compound (130 mg, 63%) as a white solid. 1H NMR (CDCl3) δ 1.63–1.66 (m, 1H), 1.97–2.07 (m, 2H), 2.25–2.27 (m, 1H), 2.66–2.72 (m, 1H), 2.80–2.85 (m, 1H), 3.65 (d, 1H, J=14 Hz), 3.71 (d, 1H, J=14 Hz), 5.03 (d, 1H, J=16 Hz), 4.14 (dd, 1H, J=9, 7 Hz), 4.21 (d, 1H, J=16 Hz), 7.11–7.19 (m, 3H), 7.41–7.48 (m, 6H), 7.65 (br d, 1H, J=5 Hz), 8.18 (s, 1H), 8.67 (dd, 1H, J=5, 1 Hz); 13C NMR (CDCl3) δ 22.2, 23.9, 30.2, 49.5, 55.0, 61.2, 112.1, 119.4, 122.7, 123.3, 127.8, 130.1, 133.0, 136.2, 138.7, 141.4, 147.8, 150.0, 156.2, 157.7. ES-MS m/z 412 (M+H). Anal. Calcd. for C25H25N5O.0.4H2O.0.3CH2Cl2: C, 68.41; H, 5.99; N, 15.77. Found: C, 68.57; H, 5.86; N, 15.48.

Aufarbeitung

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted with CH2Cl2 (3×10 mL)
  3. washthe combined organic extracts were washed once with brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification of the crude material by flash chromatography (silica gel, 75:1:1 CH2Cl2MeOH/NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-06ce467704a54a0da0b610410266fe46
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091217B2

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