Isopropanol → 5-chloro-1,3-dihydro-3-(2-oxopropyl)-1-(4-piperidinyl)-2H-benzimidazol-2-one hydrochloride

HRID 1729796Notes

Reaction equation

HRID 1729796 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]2[N:6]([CH:13]3[CH2:18][CH2:17][N:16](C(OCC)=O)[CH2:15][CH2:14]3)[C:7](=[O:12])[N:8]([CH2:9][C:10]#[CH:11])[C:4]=2[CH:3]=1.[OH-].[K+].CC([OH:31])C>O>[ClH:1].[Cl:1][C:2]1[CH:25]=[CH:24][C:5]2[N:6]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[C:7](=[O:12])[N:8]([CH2:9][C:10](=[O:31])[CH3:11])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 21500259ethyl 4-[5-chloro-1,3-dihydro-2-oxo-3-(2-propynyl)-2H-benzimidazol-1-yl]-1-piperidinecarboxylate

Product 1

HCID 215002935-chloro-1,3-dihydro-3-(2-oxopropyl)-1-(4-piperidinyl)-2H-benzimidazol-2-one hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 14 parts of ethyl 4-[5-chloro-1,3-dihydro-2-oxo-3-(2-propynyl)-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. After cooling, the solvent is evaporated and water is added to the residue. The product is extracted with methylbenzene. The extract is dried, filtered and evaporated. The oily residue is converted into the hydrochloride salt in 2,2'-oxybispropane and 2-propanol. The salt is filtered off and crystallized from ethanol, yielding 5-chloro-1,3-dihydro-3-(2-oxopropyl)-1-(4-piperidinyl)-2H-benzimidazol-2-one hydrochloride.

Workup

  1. temperaturerefluxed overnight
  2. temperatureAfter cooling
  3. customthe solvent is evaporated
  4. additionwater is added to the residue
  5. extractionThe product is extracted with methylbenzene
  6. customThe extract is dried
  7. filtrationfiltered
  8. customevaporated
  9. filtrationThe salt is filtered off
  10. customcrystallized from ethanol

Sources & evidence

ORD record
ord-43978ea7f44047f7a15504de23563666
Source dataset
uspto-grants-1976_11
Patent number
US03989707

Reaction notes

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