Hydrochloric Acid → Bilastine

HRID 384015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 384015
CC1(C)C[O:5][C:4]([C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH:21]([C:24]4[N:28]([CH2:29][CH2:30][O:31][CH2:32][CH3:33])[C:27]5[CH:34]=[CH:35][CH:36]=[CH:37][C:26]=5[N:25]=4)[CH2:20][CH2:19]3)=[CH:12][CH:11]=2)([CH3:9])[CH3:8])=N1.Cl.[OH-].[Na+].C([O:44]C(=O)C)C>C(O)CCC>[CH2:32]([O:31][CH2:30][CH2:29][N:28]1[C:27]2[CH:34]=[CH:35][CH:36]=[CH:37][C:26]=2[N:25]=[C:24]1[CH:21]1[CH2:20][CH2:19][N:18]([CH2:17][CH2:16][C:13]2[CH:12]=[CH:11][C:10]([C:7]([CH3:9])([CH3:8])[C:4]([OH:44])=[O:5])=[CH:15][CH:14]=2)[CH2:23][CH2:22]1)[CH3:33]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 404670312-(1-(2-(4-(1-(4,5-Dihydro-4,4-dimethyl-2-oxazolyl)-1-methylethyl)phenyl)ethyl)-4-piperidinyl)-1-(2-ethoxyethyl)-1H-benzimidazole

Produkt 1

HCID 185460BilastineAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

In a reaction vessel, 2-[1-(2-{4-[1-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-1-methyl-ethyl]-phenyl}-ethyl)-piperidin-4-yl]-1-(2-ethoxy-ethyl)-1H-benzoimidazole (4.4 g) prepared in the Example 18 and hydrochloric acid aqueous solution (50 mL) were introduced, and the mixture was stirred with reflux. After the reaction was completed, sodium hydroxide solution was added to control the pH to 7. Ethylacetate (50 mL) was added to separate a layer, and the organic layer was condensed under reduced pressure. And, butanol (9 mL) was added and dissolved by heating. And then, it was cooled to precipitate crystals, and the crystals were filtered under reduced pressure to obtain 2-[4-(2-{4-[1-(2-ethoxy-ethyl)-1H-benzoimidazol-2-yl]-piperidin-1-yl}-ethyl)-phenyl]-2-methyl-propionic acid (3.43 g, yield 87%, HPLC purity 99% or more).

Aufarbeitung

  1. additionwere introduced
  2. temperaturewith reflux
  3. customto separate a layer
  4. customcondensed under reduced pressure
  5. dissolutiondissolved
  6. temperatureby heating
  7. temperatureAnd then, it was cooled
  8. customto precipitate crystals
  9. filtrationthe crystals were filtered under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-33cbde70769248ec981896ab6a8ae84e
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367704B2

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