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Potassium Iodide → 1-{1-[3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-3-(1-methylethyl)-2H-benzimidazol-2-one

HRID 1833685
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1833685
Cl[C:2]1[CH:3]=[C:4]([N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10](C(C)=C)[C:9]2=[O:20])C=CC=1.[CH3:21][CH:22]([N:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[N:26]([CH:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[C:25]1=[O:39])[CH3:23].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[O:20]=[C:9]1[N:8]([CH2:4][CH2:3][CH2:2][N:36]2[CH2:37][CH2:38][CH:33]([N:26]3[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[N:24]([CH:22]([CH3:21])[CH3:23])[C:25]3=[O:39])[CH2:34][CH2:35]2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[NH:10]1
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Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 186959941-(1-methylethyl)-3-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 21389817HCID 21389817, Verbindung

Produkt 1

HCID 203855711-{1-[3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-3-(1-methylethyl)-2H-benzimidazol-2-oneAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 7909Methyl Isobutyl KetoneLösungsmittel

Versuchsvorschrift

A mixture of 4.15 parts of 1-(3-chlorophenyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one, 3.9 parts of 1-(1-methylethyl)-3-(4-piperidinyl)-2H-benzimidazol-2-one, 3.2 parts of sodium carbonate, 0.1 parts of potassium iodide and 120 parts of 4-methyl-2-pentanone is stirred and refluxed overnight. The reaction mixture is cooled to room temperature, water is added and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is stirred for 30 minutes with a solution of 12 parts of a concentrated hydrochloric acid solution in 40 parts of ethanol. The solvent is evaporated and the residue is suspended in water. The suspension is alkalized with a diluted ammonium hydroxide solution and the product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 4-methyl-2-pentanone. The product is filtered off and dried, yielding 4.2 parts (64%) of 1-{1-[3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-3-(1-methylethyl)-2H-benzimidazol-2-one; mp. 174.3° C.

Aufarbeitung

  1. temperaturerefluxed overnight
  2. customthe layers are separated
  3. customThe organic phase is dried
  4. filtrationfiltered
  5. customevaporated
  6. stirringThe residue is stirred for 30 minutes with a solution of 12 parts of a concentrated hydrochloric acid solution in 40 parts of ethanol
  7. customThe solvent is evaporated
  8. extractionthe product is extracted with trichloromethane
  9. customThe extract is dried
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue is purified by column-chromatography over silica gel using
  13. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  14. customThe pure fractions are collected
  15. customthe eluent is evaporated
  16. customThe residue is crystallized from 4-methyl-2-pentanone
  17. filtrationThe product is filtered off
  18. customdried

Quellen und Nachweise

ORD-Eintrag
ord-de8cd0ff231c4f1896c8318219a90f8c
Quelldatensatz
uspto-grants-1978_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04066772

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