Acetic Acid → N-[2-(4-(imidazol-1-yl)phenoxy)ethyl]-N-[(1,3-benzodioxol-5-yl)methyl]amine

HRID 1609819Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1609819
[N:1]1([C:6]2[CH:15]=[CH:14][C:9]([O:10][CH2:11][CH2:12][NH2:13])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[CH:16]1[C:21]([CH:22]=O)=[CH:20][C:19]2[O:24][CH2:25][O:26][C:18]=2[CH:17]=1.C(O)(=O)C.[BH3-]C#N.[Na+]>CO>[N:1]1([C:6]2[CH:15]=[CH:14][C:9]([O:10][CH2:11][CH2:12][NH:13][CH2:22][C:21]3[CH:16]=[CH:17][C:18]4[O:26][CH2:25][O:24][C:19]=4[CH:20]=3)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 8438PiperonalHCID 5003444Sodium cyanoborohydrideHCID 145556572-[4-(Imidazol-1-yl)phenoxy]ethylamine

Produkt 1

HCID 10019960N-[2-(4-(imidazol-1-yl)phenoxy)ethyl]-N-[(1,3-benzodioxol-5-yl)methyl]amineAusbeute 51,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To 2-[4-(imidazol-1-yl)phenoxy]ethylamine (4.0 g, 20 mmol) dissolved in MeOH (150 mL) was added piperonal (3.0 g, 20 mmol) and acetic acid (1.5 mL). After stirring for 1 h, NaBH3CN (2.6 g, 40 mmol) was added. After stirring for 18 hour, the solvent was removed in vacuo and the residue was chromatographed on silical gel with 2% methanol in methylene chloride to give 3.5 g of N-[2-(4-(imidazol-1-yl)phenoxy)ethyl]-N-[(1,3-benzodioxol-5-yl)methyl]amine, 1H NMR (DMSO-d6) 8.12 (s, 1), 7.62 (s, 1), 7.54 (d, 2), 7.08-7.02 (m, 3), 6.90 (s, 1), 6.82-6.75 (m, 2), 5.94 (s, 2), 4.03 (t, 2), 3.62 (s, 2), 3.32 (s, 1), 2.80 (t, 2) ppm.

Aufarbeitung

  1. stirringAfter stirring for 18 hour
  2. customthe solvent was removed in vacuo
  3. customthe residue was chromatographed on silical gel with 2% methanol in methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-05dd5823ee094afdbc4b1034fbf6f1ad
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06982259B2

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