Potassium Iodide → 6-chloro-1{1-[4,4-bis(4-fluorophenyl)butyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one 2-propanolate

HRID 1729812Notes

Reaction equation

HRID 1729812 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:6]=2[CH:17]=1.C(=O)([O-])[O-:19].[Na+].[Na+].[I-].[K+].Cl[CH2:27][CH2:28][CH2:29][CH:30]([C:38]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=1)[C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=1>O.CC(C)CC(=O)C>[CH3:2][CH:17]([O-:19])[CH3:6].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([CH:11]3[CH2:12][CH2:13][N:14]([CH2:27][CH2:28][CH2:29][CH:30]([C:31]4[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=4)[C:38]4[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=4)[CH2:15][CH2:16]3)[C:6]=2[CH:17]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 137921086-Chloro-1-piperidin-4-yl-1,3-dihydro-benzoimidazol-2-one

Product 1

HCID 215002436-chloro-1{1-[4,4-bis(4-fluorophenyl)butyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one 2-propanolate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 5 parts of 6-chloro-1,3-dihydro-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 for awhile, there are added 7 parts of 1-chloro-4,4-bis(4-fluorophenyl)-butane and stirring at reflux is continued for 20 hours. The reaction mixture is cooled, water is added and the layers are separated. The organic layer is dried, filtered and evaporated. The oily residue is acidified with a diluted hydrochloric acid solution. After shaking thoroughly with toluene, the latter is decanted and discarded. The aqueous acid phase, together with the residual oil, is alkalized with ammonium hydroxide and the product is extracted with toluene. The extract is dried, filtered and evaporated. The oily residue is crystallized from 2-propanol, yielding 6-chloro-1{1-[4,4-bis(4-fluorophenyl)butyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one 2-propanolate; mp. 174.6° C.

Workup

  1. temperatureAfter cooling for awhile, there
  2. stirringstirring
  3. temperatureat reflux
  4. temperatureThe reaction mixture is cooled
  5. customthe layers are separated
  6. customThe organic layer is dried
  7. filtrationfiltered
  8. customevaporated
  9. stirringAfter shaking thoroughly with toluene
  10. customthe latter is decanted
  11. extractionthe product is extracted with toluene
  12. customThe extract is dried
  13. filtrationfiltered
  14. customevaporated
  15. customThe oily residue is crystallized from 2-propanol

Sources & evidence

ORD record
ord-8890f45244ab478197936f0f42196449
Source dataset
uspto-grants-1976_11
Patent number
US03989707

Reaction notes

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