Potassium Iodide → Diisopropyl Ether

HRID 1729827Notes

Reaction equation

HRID 1729827 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[N:6]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[C:7](=[O:16])[N:8]([CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:4]=2[CH:3]=1.C(=O)([O-])[O-:26].[Na+].[Na+].[I-].[K+].Cl[CH2:34][CH2:35][CH2:36][CH:37]([C:45]1[CH:50]=[CH:49][C:48]([F:51])=[CH:47][CH:46]=1)[C:38]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=1>O.CC(C)CC(=O)C>[O:26]([CH:24]([CH3:23])[CH3:2])[CH:35]([CH3:36])[CH3:34].[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[N:6]([CH:17]3[CH2:18][CH2:19][N:20]([CH2:34][CH2:35][CH2:36][CH:37]([C:38]4[CH:39]=[CH:40][C:41]([F:44])=[CH:42][CH:43]=4)[C:45]4[CH:50]=[CH:49][C:48]([F:51])=[CH:47][CH:46]=4)[CH2:21][CH2:22]3)[C:7](=[O:16])[N:8]([CH2:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 21500279HCID 21500279, compound

Product 2

HCID 7914Diisopropyl EtherHCID 21500256HCID 21500256, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 6.8 parts of 5-chloro-1,3-dihydro-3-(phenylmethyl)-1-(4-piperidinyl)-2H-benzimidazol-2-one, 6.4 parts of sodium carbonate, 0.1 parts of potassium iodide and 200 parts of 4-methyl-2-pentanone is stirred and refluxed for 30 minutes with water-separator. After cooling, 7 parts of 1-chloro-4,4-bis(4-fluorophenyl)butane are added 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 crystallized twice: first from 2,2'-oxybispropane and then from 2-propanol, yielding 5-chloro-1-{1-[4,4-bis(4-fluorophenyl)butyl]-4-piperidinyl}-1,3-dihydro-3-(phenylmethyl)-2H-benzimidazol-2-one; mp. 141.5° 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 crystallized twice

Sources & evidence

ORD record
ord-3233e26ac1254ff4a9eabfed5e5f0365
Source dataset
uspto-grants-1976_11
Patent number
US03989707

Reaction notes

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