Potassium Iodide → 5-chloro-1-{1-[4,4-bis(4-fluorophenyl)butyl]-4-piperidinyl}-1,3-dihydro-3-methyl-2H-benzimidazol-2-one

HRID 1729828Notes

Reaction equation

HRID 1729828 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:7](=[O:10])[N:8]([CH3:9])[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].Cl[CH2:28][CH2:29][CH2:30][CH:31]([C:39]1[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=1)[C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=1>O.CC(C)CC(=O)C>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]([CH:11]3[CH2:12][CH2:13][N:14]([CH2:28][CH2:29][CH2:30][CH:31]([C:32]4[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=4)[C:39]4[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=4)[CH2:15][CH2:16]3)[C:7](=[O:10])[N:8]([CH3:9])[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 214934435-chloro-3-methyl-1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one

Product 1

HCID 215002925-chloro-1-{1-[4,4-bis(4-fluorophenyl)butyl]-4-piperidinyl}-1,3-dihydro-3-methyl-2H-benzimidazol-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 5,3 parts of 5-chloro-1,3-dihydro-3-methyl-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 30 minutes with water-separator. After cooling, there are added 7 parts of 1-chloro-4,4-bis(4-fluorophenyl)-butane and stirring at reflux temperature is continued overnight. The reaction mixture is cooled, water is added and the layers are separated. The organic phase is dried, filtered and evaporated. The oily residue is triturated in 2,2'-oxybispropane. The product is filtered off, dried and crystallized from 2-propanol, yielding 5-chloro-1-{1-[4,4-bis(4-fluorophenyl)butyl]-4-piperidinyl}-1,3-dihydro-3 -methyl-2H-benzimidazol-2-one; mp. 155.8° C.

Workup

  1. temperatureAfter cooling
  2. stirringstirring
  3. temperatureat reflux temperature
  4. temperatureThe reaction mixture is cooled
  5. customthe layers are separated
  6. customThe organic phase is dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe oily residue is triturated in 2,2'-oxybispropane
  10. filtrationThe product is filtered off
  11. customdried
  12. customcrystallized from 2-propanol

Sources & evidence

ORD record
ord-b6a3d365b8d646958dc9d8f2261b2f63
Source dataset
uspto-grants-1976_11
Patent number
US03989707

Reaction notes

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