Potassium Iodide → 1-{3-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]propyl}-1,3-dihydro-5,6-dimethyl-2H-benzimidazol-2-one hydrochloride

HRID 1833656

Reaktionsgleichung

Reaktionsgleichung von HRID 1833656
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[C:11]([CH3:15])[C:12]([CH3:14])=[CH:13][C:8]=2[NH:7][C:6]1=[O:16].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2([OH:30])[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[ClH:1].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2([OH:30])[CH2:25][CH2:26][N:27]([CH2:2][CH2:3][CH2:4][N:5]3[C:9]4[CH:10]=[C:11]([CH3:15])[C:12]([CH3:14])=[CH:13][C:8]=4[NH:7][C:6]3=[O:16])[CH2:28][CH2:29]2)=[CH:20][CH:19]=1

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 203856481-(3-chloropropyl)-1,3-dihydro-5,6-dimethyl-2H-benzimidazol-2-one

Produkt 1

HCID 203856421-{3-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]propyl}-1,3-dihydro-5,6-dimethyl-2H-benzimidazol-2-one hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 7909Methyl Isobutyl KetoneLösungsmittel

Versuchsvorschrift

A mixture of 3.58 parts of 1-(3-chloropropyl)-1,3-dihydro-5,6-dimethyl-2H-benzimidazol-2-one, 3.17 parts of 4-(4-chlorophenyl)-4-piperidinol, 5.3 parts of sodium carbonate, 0.2 parts of potassium iodide and 160 parts of 4-methyl-2-pentanone is stirred and refluxed for 24 hours with water-separator. After cooling, water is added and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is converted into the hydrochloride salt in methanol and 2-propanol. The salt is filtered off and dried, yielding 1.7 parts of 1-{3-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]propyl}-1,3-dihydro-5,6-dimethyl-2H-benzimidazol-2-one hydrochloride; mp. 260.8° C.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe layers are separated
  3. customThe organic phase is dried
  4. filtrationfiltered
  5. customevaporated
  6. filtrationThe salt is filtered off
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5ab363a3e78b452e98eee928ad8d039e
Quelldatensatz
uspto-grants-1978_01
Patentnummer
US04066772

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