Potassium Iodide → HCID 21500285, compound

HRID 1729826Notes

Reaction equation

HRID 1729826 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.[Cl:20][C:21]1[CH:40]=[CH:39][C:24]2[N:25]([CH:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)[C:26](=[O:32])[N:27]([CH2:28][C:29](=[O:31])[CH3:30])[C:23]=2[CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[Cl:20][C:21]1[CH:40]=[CH:39][C:24]2[N:25]([CH:33]3[CH2:34][CH2:35][N:36]([CH2:2][CH2:3][CH2:4][CH:5]([C:13]4[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=4)[C:6]4[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=4)[CH2:37][CH2:38]3)[C:26](=[O:32])[N:27]([CH2:28][C:29](=[O:31])[CH3:30])[C:23]=2[CH:22]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 21500294HCID 21500294, compound

Product 1

HCID 21500285HCID 21500285, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 7 parts of 1-chloro-4,4-bis(4-fluorophenyl)-butane, 5 parts of 5-chloro-1,3-dihydro-3-(2-oxopropyl)-1-(4-piperidinyl)-2H-benzimidazol-2-one, 6.4 parts of sodium carbonate, 0.2 parts of potassium iodide and 160 parts of 4-methyl-2-pentanone is stirred and refluxed for 24 hours. After cooling, water is added and the layers are separated. The organic phase is dried, filtered and evaporated. The oily residue is stirred while warming in 2,2'-oxybispropane. The turbid mixture is filtered hot over hyflo and the clear filtrate is allowed to cool to room temperature while stirring. The crystallized product is filtered off and recrystallized from 2-propanol, yielding 5-chloro-1-{1 -[4,4-bis(4-fluorophenyl)butyl]-4-piperidinyl}-1,3-dihydro-3 -(2-oxopropyl)-2H-benzimidazol-2-one; mp. 175.3° C.

Workup

  1. temperaturerefluxed for 24 hours
  2. temperatureAfter cooling
  3. customthe layers are separated
  4. customThe organic phase is dried
  5. filtrationfiltered
  6. customevaporated
  7. stirringThe oily residue is stirred
  8. temperaturewhile warming in 2,2'-oxybispropane
  9. filtrationThe turbid mixture is filtered hot over hyflo
  10. stirringwhile stirring
  11. filtrationThe crystallized product is filtered off
  12. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-da086498d0ec429997c76b58b6d1aad7
Source dataset
uspto-grants-1976_11
Patent number
US03989707

Reaction notes

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