Dimethylformamide → 1-[(1-Carbomethoxy methoxy ethyl)-1H-benzimidazol-2-yl][1-(t-butyloxycarbonyl)-4-piperidinyl]methanone

HRID 1769034Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1769034
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)=[O:11].[C:25]([CH2:29][O:30][CH2:31][CH2:32]Br)([O:27][CH3:28])=[O:26].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:25]([CH2:29][O:30][CH:31]([N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:12]1[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]1)=[O:11])[CH3:32])([O:27][CH3:28])=[O:26]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 183332351-(t-butoxycarbonyl)-4-(1H-benzimidazole-2-carbonyl)piperidineHCID 18946503Methyl (2-bromoethoxy)acetate

Produkt 1

HCID 542868801-[(1-Carbomethoxy methoxy ethyl)-1H-benzimidazol-2-yl][1-(t-butyloxycarbonyl)-4-piperidinyl]methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Mix [1H-benzimidazol-2-yl][1-(t-butyloxycarbonyl)-4-piperidinyl]methanone (4.25 g, 12.91 mmol), carbomethoxy methoxy ethylbromide (3.01 g, 15.3 mmol), potassium carbonate (5.29 g, 38.25 mmol) and dimethylformamide (100 mL). Stir and heat and at 90° C. overnight. Allow to cool to room temperature, dilute with water and extract with ethyl acetate (2×). Wash the combined organic phases with water (3×), then brine and dry (MgSO4). Evaporate the solvent in vacuo to give and purify by chromatography to give the title compound.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. extractionextract with ethyl acetate (2×)
  3. washWash the combined organic phases with water (3×)
  4. dry with materialbrine and dry (MgSO4)
  5. customEvaporate the solvent in vacuo
  6. customto give
  7. custompurify by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9334016447e24a608f1a4d35e3b23c7b
Quelldatensatz
uspto-grants-1995_01
Patentnummer
US05380731

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