Sodium Hydroxide → 5-Chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one

HRID 2417795

Reaction equation

HRID 2417795 reaction equation
C([N:6]1[CH2:11][CH2:10][CH:9]([N:12]2[C:16]3[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:15]=3[NH:14][C:13]2=[O:22])[CH2:8][CH2:7]1)(OCC)=O.[OH-].[Na+].[Cl-].[NH4+]>O>[Cl:21][C:19]1[CH:18]=[CH:17][C:16]2[N:12]([CH:9]3[CH2:8][CH2:7][NH:6][CH2:11][CH2:10]3)[C:13](=[O:22])[NH:14][C:15]=2[CH:20]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 104610Ethyl 4-(5-chloro-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinecarboxylate

Product 1

HCID 1046075-Chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 22.3 g of 1-carbethoxy-4-(5-chlorobenzimidazol-2-on-1-yl)-piperidine, 13 g of 50% strength sodium hydroxide solution and 90 ml of water was boiled under reflux for 24 hours. After the mixture had been cooled, the solution was stirred with 8.5 g of ammonium chloride for 30 minutes and extracted with chloroform, and the undissolved material was filtered off and discarded. The chloroform solution was dried and evaporated. The product crystallized, and has a melting point of 220° C.

Workup

  1. temperatureunder reflux for 24 hours
  2. temperatureAfter the mixture had been cooled
  3. extractionextracted with chloroform
  4. filtrationthe undissolved material was filtered off
  5. dry with materialThe chloroform solution was dried
  6. customevaporated
  7. customThe product crystallized

Sources & evidence

ORD record
ord-81f7d53e494e42f0a6b69705f54f78bd
Source dataset
uspto-grants-1984_09
Patent number
US04470989

Linked notes

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