Potassium Iodide → HCID 21500298, compound

HRID 1729814Notes

Reaction equation

HRID 1729814 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH:5]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.[I:20][C:21]1[CH:36]=[CH:35][C:24]2[N:25]([CH:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[C:26](=[O:28])[NH:27][C:23]=2[CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[F:12][C:9]1[CH:10]=[CH:11][C:6]([CH:5]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:4][CH2:3][CH2:2][N:32]2[CH2:31][CH2:30][CH:29]([N:25]3[C:24]4[CH:35]=[CH:36][C:21]([I:20])=[CH:22][C:23]=4[NH:27][C:26]3=[O:28])[CH2:34][CH2:33]2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 21500245HCID 21500245, compound

Product 1

HCID 21500298HCID 21500298, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 7 parts of 1-chloro-4,4-bis(4-fluorophenyl)-butane, 6.84 parts of 1,3-dihydro-5-iodo-1-(4-piperidinyl)-2H-benzimidazol-2-one, 6.4 parts of sodium carbonate, 0.2 parts of potassium iodide and 200 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 purified by column-chromatography over silicagel, using a mixture of trichloromethane and 5% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from a mixture of 2,2'-oxybispropane and 2-propanol, yielding 1-{1-[4,4-bis(4-fluorophenyl)-butyl]-4-piperidinyl}-1,3-dihydro-5 -iodo-2H-benzimidazol-2-one; mp. 179.3° C.

Workup

  1. temperatureAfter cooling
  2. customthe layers are separated
  3. customThe organic phase is dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by column-chromatography over silicagel
  7. additiona mixture of trichloromethane and 5% of methanol as eluent
  8. customThe pure fractions are collected
  9. customthe eluent is evaporated
  10. customThe residue is crystallized from a mixture of 2,2'-oxybispropane and 2-propanol

Sources & evidence

ORD record
ord-f3aff7abe1954a16a73b2a9e7dd6160b
Source dataset
uspto-grants-1976_11
Patent number
US03989707

Reaction notes

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