Sodium Hydroxide → Ethyl[1-{1-[(4-fluorophenyl)-methyl]-1H-benzimidazol-2-yl}-4-piperidyl]carbamate

HRID 1165920Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1165920
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:13])[O:10][CH2:11][CH3:12])[CH2:4][CH2:3]1.C[O-].[Na+].Cl[C:18]1[N:22]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[C:21]2[CH:31]=[CH:32][CH:33]=[CH:34][C:20]=2[N:19]=1.[OH-].[Na+]>CO.C(Cl)Cl>[CH2:11]([O:10][C:9](=[O:13])[NH:8][CH:5]1[CH2:4][CH2:3][N:2]([C:18]2[N:22]([CH2:23][C:24]3[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=3)[C:21]3[CH:31]=[CH:32][CH:33]=[CH:34][C:20]=3[N:19]=2)[CH2:7][CH2:6]1)[CH3:12]

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 30202411-(4-Fluorobenzyl)-2-chlorobenzimidazoleHCID 10942334Sodium MethoxideHCID 19861299Ethyl piperidin-4-ylcarbamate hydrochloride

Produkt 1

HCID 15595031Ethyl[1-{1-[(4-fluorophenyl)-methyl]-1H-benzimidazol-2-yl}-4-piperidyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

19 g (0.09 mole) of ethyl 4-piperidylcarbamate hydrochloride is solubilized in 120 ml of methanol and neutralized with 17.2 ml of 5.3N sodium methylate. The mixture is filtered and the filtrate evaporated to dryness. The evaporation residue is then mixed with 21.6 g (0.083 mole) of 2-chloro-1-[(4-fluorophenyl)methyl]-1H-benzimidazole and heated to 140° C. for 5 hours. The reaction mass is taken up with methylene chloride and alkalinized with 2N sodium hydroxide. The organic phase is washed with water, dried, filtered and evaporated. The oil obtained is chromatographed on silica (eluent: methylene chloride/methanol, 97.5:2.5). Ethyl[1-{1-[(4-fluorophenyl)-methyl]-1H-benzimidazol-2-yl}-4-piperidyl]carbamate is obtained.

Aufarbeitung

  1. filtrationThe mixture is filtered
  2. customthe filtrate evaporated to dryness
  3. washThe organic phase is washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe oil obtained
  8. customis chromatographed on silica (eluent: methylene chloride/methanol, 97.5:2.5)

Quellen und Nachweise

ORD-Eintrag
ord-571380de5f4c497b8cb3777447036cb8
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04912219

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