Hydrochloric Acid → 4-[3-(1-Methyl-1H-benzoimidazol-2-yl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 2047372Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2047372
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[NH:24][C:23]4[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=4[N:21]=3)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:31]I.Cl>C1COCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[N:21]([CH3:31])[C:22]4[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=4[N:24]=3)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 595680504-[3-(1H-Benzoimidazol-2-yl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 595682004-[3-(1-Methyl-1H-benzoimidazol-2-yl)-phenyl]-piperazine-1-carboxylic acid tert-butyl esterAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 4-[3-(1H-benzoimidazol-2-yl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester (0.83 g, 2.20 mmol) (obtained as described in method B) and NaH 60% oil (0.11 g, 4.39 mmol) in THF (10 mL) was stirred at room temperature for 1 h. Methyl iodide (0.27 mL, 4.39 mmol) was added and the resulting solution was stirred overnight. Water (15 mL) was added to the reaction solution, then the suspension was neutralized with 1N HCl and extracted with EtOAc (3×40 mL) The combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was triturated with Et2O and the solid obtained filtered, to give 0.76 g (88%) of the title compound.

Aufarbeitung

  1. stirringthe resulting solution was stirred overnight
  2. extractionextracted with EtOAc (3×40 mL) The combined organic layers
  3. dry with materialwere dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated with Et2O
  7. customthe solid obtained
  8. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-1fb32b10416c44fa9d6d8c1bbd9418f4
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592463B2

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