Isopropanol → 5-chloro-3-methyl-1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one

HRID 1729794Notes

Reaction equation

HRID 1729794 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]([CH:11]3[CH2:16][CH2:15][N:14](C(OCC)=O)[CH2:13][CH2:12]3)[C:7](=[O:10])[N:8]([CH3:9])[C:4]=2[CH:3]=1.[OH-].[K+].CC(O)C>O>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]([CH:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]3)[C:7](=[O:10])[N:8]([CH3:9])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 21500268ethyl 4-(5-chloro-1,3-dihydro-3-methyl-2-oxo-2H-benzimidazol-1-yl)-1-piperidinecarboxylate

Product 1

HCID 214934435-chloro-3-methyl-1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 12.8 parts of ethyl 4-(5-chloro-1,3-dihydro-3-methyl-2-oxo-2H-benzimidazol-1-yl)-1-piperidinecarboxylate, 20 parts of potassium hydroxide, 128 parts of 2-propanol and 2.5 parts of water is stirred and refluxed overnight. The reaction mixture is cooled and evaporated. Water is added to the residue and the product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is triturated in 2,2'-oxybispropane. The product is filtered off and dried, yielding 5-chloro-1,3-dihydro-3-methyl-1-(4-piperidinyl)-2H-benzimidazol-2-one; mp. 200.9° C.

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe reaction mixture is cooled
  3. customevaporated
  4. additionWater is added to the residue
  5. extractionthe product is extracted with trichloromethane
  6. customThe extract is dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is triturated in 2,2'-oxybispropane
  10. filtrationThe product is filtered off
  11. customdried

Sources & evidence

ORD record
ord-140f30a72b28490297b55561360531a7
Source dataset
uspto-grants-1976_11
Patent number
US03989707

Reaction notes

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