Methyl Isobutyl Ketone → 1-{1-[3-(1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-5-chloro-1,3-dihydro-2H-benzimidazol-2-one

HRID 46906

Reaktionsgleichung

Reaktionsgleichung von HRID 46906
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[CH:6]1.[Cl:14][C:15]1[CH:30]=[CH:29][C:18]2[N:19]([CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[C:20](=[O:22])[NH:21][C:17]=2[CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].CC(C)CC(=O)C>O>[N:5]1([CH2:4][CH2:3][CH2:2][N:26]2[CH2:25][CH2:24][CH:23]([N:19]3[C:18]4[CH:29]=[CH:30][C:15]([Cl:14])=[CH:16][C:17]=4[NH:21][C:20]3=[O:22])[CH2:28][CH2:27]2)[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[CH:6]1

Komponenten

6

Edukt 4

HCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 1046075-Chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 131055171-(3-Chloropropyl)-1H-benzimidazole

Produkt 1

HCID 203855791-{1-[3-(1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-5-chloro-1,3-dihydro-2H-benzimidazol-2-oneAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 9 parts of 1-(3-chloropropyl)-1H-benzimidazole, 10 parts of 5-chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one, 7.4 parts of sodium carbonate and 200 parts of 4-methyl-2-pentanone is stirred and refluxed overnight. The reaction mixture is cooled, water is added and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is crystallized from 4-methyl-2-pentanone, yielding 2.9 parts (14%) of 1-{1-[3-(1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-5-chloro-1,3-dihydro-2H-benzimidazol-2-one; mp. 224° C.

Aufarbeitung

  1. temperaturerefluxed overnight
  2. temperatureThe reaction mixture is cooled
  3. customthe layers are separated
  4. customThe organic phase is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is crystallized from 4-methyl-2-pentanone

Quellen und Nachweise

ORD-Eintrag
ord-e14ae101c17d401ab38a545c8ba86135
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04175129

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