Potassium Iodide → HCID 20288037, compound

HRID 126870Notes

Reaction equation

HRID 126870 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:13].Cl.[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:30])[CH2:23][CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:30])[CH2:23][CH:24]2[CH2:29][CH2:28][N:27]([CH2:2][CH2:3][N:4]3[C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=4[NH:6][C:5]3=[O:13])[CH2:26][CH2:25]2)=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 36534711-(2-Chloroethyl)-1,3-dihydro-2H-benzimidazol-2-oneHCID 20288069HCID 20288069, compound

Product 1

HCID 20288037HCID 20288037, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 2.16 parts of 1-(2-chloroethyl)-1,3-dihydro-2H-benzimidazol-2-one, 2.57 parts of 1-(4-fluorophenyl)-2-(4-piperidinyl)ethanone hydrochloride, 5.3 parts of sodium carbonate, 0.2 parts of potassium iodide and 200 parts of 4-methyl-2-pentanone is stirred and refluxed for 15 hours using a water-separator. The reaction mixture is cooled, water is added and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is crystallized from a mixture of 2,2'-oxybispropane and 2-propanol. The product is filtered off and dried, yielding 2.5 parts of 1-[2-[4-[2-(4-fluorophenyl)-2-oxoethyl]-1-piperidinyl]ethyl]-1,3-dihydro-2H-benzimidazol-2-one; mp. 180.6° C.

Workup

  1. temperaturerefluxed for 15 hours
  2. temperatureThe reaction mixture is cooled
  3. customthe layers are separated
  4. customThe organic phase is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is crystallized from a mixture of 2,2'-oxybispropane and 2-propanol
  8. filtrationThe product is filtered off
  9. customdried

Sources & evidence

ORD record
ord-173e6664430d41d9ae34feea31fb7027
Source dataset
uspto-grants-1981_03
Patent number
US04254127

Reaction notes

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