Potassium Iodide → 5-chloro-1,3-dihydro-1-[1-(4,4-diphenylbutyl)-4-piperidinyl]-2-H-benzimidazol-2-one

HRID 1729820Notes

Reaction equation

HRID 1729820 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl:18][C:19]1[CH:34]=[CH:33][C:22]2[N:23]([CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[C:24](=[O:26])[NH:25][C:21]=2[CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[Cl:18][C:19]1[CH:34]=[CH:33][C:22]2[N:23]([CH:27]3[CH2:28][CH2:29][N:30]([CH2:2][CH2:3][CH2:4][CH:5]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:6]4[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH2:31][CH2:32]3)[C:24](=[O:26])[NH:25][C:21]=2[CH:20]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 768211,1'-(4-Chlorobutylidene)bisbenzeneHCID 1046075-Chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one

Product 1

HCID 215002485-chloro-1,3-dihydro-1-[1-(4,4-diphenylbutyl)-4-piperidinyl]-2-H-benzimidazol-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 7.35 parts of 1-chloro-4,4-diphenylbutane, 6.3 parts of 5-chloro-1-(4-piperidyl)-2-benzimidazolinone, 6.35 parts of sodium carbonate, 0.1 parts of potassium iodide and 200 parts of 4-methyl-2-pentanone is stirred and refluxed for 48 hours with water-separator. The reaction mixture is cooled to room temperature and water is added. The organic layer is separated, dried, filtered and evaporated. The residue is crystallized twice; first from 2-propanol and then from 4-methyl-2-pentanone, yielding 5-chloro-1,3-dihydro-1-[1-(4,4-diphenylbutyl)-4-piperidinyl]-2-H-benzimidazol-2-one; mp. 164.7° C.

Workup

  1. customThe organic layer is separated
  2. customdried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue is crystallized twice

Sources & evidence

ORD record
ord-9915b96491b245c1b203fdebb92d327a
Source dataset
uspto-grants-1976_11
Patent number
US03989707

Reaction notes

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