Potassium Iodide → HCID 21500261, compound

HRID 1729818Notes

Reaction equation

HRID 1729818 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:9][CH2:10][CH2:11]Cl)=[CH:4][CH:3]=1.[Cl:20][C:21]1[CH:22]=[CH:23][C:24]2[NH:28][C:27](=[O:29])[N:26]([CH:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[C:25]=2[C:36]=1[CH3:37].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]2[NH:28][C:27](=[O:29])[N:26]([CH:30]3[CH2:31][CH2:32][N:33]([CH2:11][CH2:10][CH2:9][CH:8]([C:13]4[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=4)[C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[CH2:34][CH2:35]3)[C:25]=2[C:36]=1[CH3:37]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 13792105HCID 13792105, compound

Product 1

HCID 21500261HCID 21500261, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 3.5 parts of 1,1-bis(4-fluorophenyl)-4-chlorobutane, 3.65 parts of 6-chloro-1,3-dihydro-7-methyl-1-(4-piperidinyl)- 2H-benzimidazol-2-one, 2.65 parts of sodium carbonate, 0.1 parts of potassium iodide and 100 parts of 4-methyl-2-pentanone is stirred and refluxed for 36 hours. After cooling to room temperature, 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 methylbenzene. The aqueous- and methylbenzene phases are decanted and discarded. From the sticky residual salt, the free base is liberated in the conventional manner and extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is crystallized from 4-methyl-2-pentanone, yielding 6-chloro-1-{1-[4,4-bis(4-fluorophenyl)butyl]-4-piperidinyl}-1,3-dihydro-7-methyl-2H-benzimidazol-2-one; mp. 171.9° C.

Workup

  1. temperaturerefluxed for 36 hours
  2. customthe layers are separated
  3. customThe organic phase is dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe aqueous- and methylbenzene phases are decanted
  7. extractionextracted with trichloromethane
  8. customThe extract is dried
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue is crystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-383a480ae8da45138eaa1191392e412e
Source dataset
uspto-grants-1976_11
Patent number
US03989707

Reaction notes

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