Potassium Iodide → HCID 21188532, compound

HRID 1384013Notes

Reaction equation

HRID 1384013 reaction equation
[CH2:1]([C:4]1[C:12]2[N:11]=[C:10]([CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[N:9]([CH2:22][CH2:23][CH2:24][CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[N:39]1([CH2:45][CH2:46][CH2:47]Cl)[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1>CN(C)C=O>[CH2:1]([C:4]1[C:12]2[N:11]=[C:10]([CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[N:9]([CH2:22][CH2:23][CH2:24][CH:25]3[CH2:26][CH2:27][N:28]([CH2:47][CH2:46][CH2:45][N:39]4[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]4)[CH2:29][CH2:30]3)[C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 79625Piperidine, 1-(3-chloropropyl)-HCID 21188464HCID 21188464, compound

Product 1

HCID 21188532HCID 21188532, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In a 25 ml round bottom flask, under a nitrogen atmosphere, were added 4-(prop-2-enyl)-2-[(4-chlorophenoxy)methyl]-1-[3-(piperidin-4-yl)propyl]benzimidazole (69.9 mg, 0.13 mmol), potassium carbonate (161.9 mg, 1.17 mmol), potassium iodide (21.6 mg, 0.13 mmol), 3-(piperidin-1-yl)propyl chloride (33.52 mg, 0.17 mmol) and N,N-dimethylformamide (3 ml). The resulting mixture was heated to 100° C. and maintained at this temperature. The progress of the reaction was monitored by thin layer chromatography. The reaction was quenched by the addition of water. The aqueous fraction was extracted wtih ethyl acetate. The organic fractions were combined, washed with water, and then dried over sodium sulfate. The solvents were removed in vacuo. The desired title product was further purified by radial chromatography.

Workup

  1. temperaturemaintained at this temperature
  2. customThe reaction was quenched by the addition of water
  3. extractionThe aqueous fraction was extracted wtih ethyl acetate
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customThe solvents were removed in vacuo
  7. customThe desired title product was further purified by radial chromatography

Sources & evidence

ORD record
ord-d43a1c4b731f42caa0422089a67f2540
Source dataset
uspto-grants-2001_07
Patent number
US06255494B1

Reaction notes

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