Potassium Iodide → HCID 23329041, compound

HRID 225135Notes

Reaction equation

HRID 225135 reaction equation
Cl[CH:2]([F:14])[CH2:3][CH:4]([OH:13])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[O:15]=[C:16]1[N:20]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[C:19]2[CH:27]=[CH:28][CH:29]=[CH:30][C:18]=2[NH:17]1.C(=O)([O-])O.[Na+].[I-].[K+]>C1(C)C=CC=CC=1>[O:15]=[C:16]1[N:20]([CH:21]2[CH2:22][CH2:23][N:24]([CH:2]([F:14])[CH2:3][CH:4]([OH:13])[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[O:6])[CH2:25][CH2:26]2)[C:19]2[CH:27]=[CH:28][CH:29]=[CH:30][C:18]=2[NH:17]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 516892Sodium BicarbonateHCID 19870779HCID 19870779, compound

Product 1

HCID 23329041HCID 23329041, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 10 g of γ-chloro-2-hydroxy-4-fluorobutyrophenone, 6.6 g of 4-(2-keto-1-benzimidazolinyl)piperidine, 2.6 g of sodium hydrogen carbonate, 0.05 g of potassium iodide and 300 ml of toluene was refluxed for 27 hours. The resulting mixture was poured into ice water and extracted with chloroform. The extract was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residual viscous oil was chromatographed over silica gel (100-200 mesh) with ethyl acetate as an eluting agent to give γ-[4-(2-keto-1-benzimidazolinyl)piperidin-1-yl]-2-hydroxy-4-fluorobutyrophenone, M.P. 175°-181° C.

Workup

  1. temperaturewas refluxed for 27 hours
  2. extractionextracted with chloroform
  3. washThe extract was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residual viscous oil was chromatographed over silica gel (100-200 mesh) with ethyl acetate as an eluting agent

Sources & evidence

ORD record
ord-0faf4e2da21c4e89bbf3db4b510fd2bb
Source dataset
uspto-grants-1980_11
Patent number
US04235914

Reaction notes

Loading…