Isopropanol → HCID 21500289, compound

HRID 1729809Notes

Reaction equation

HRID 1729809 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13](C(OC)=O)[CH:12]([CH3:20])[CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[OH-].[K+].CC(O)C>O>[ClH:1].[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][NH:13][CH:12]([CH3:20])[CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 21500249HCID 21500249, compound

Product 1

HCID 21500289HCID 21500289, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 20 parts of methyl 4-(5-chloro-1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)-2-methyl-1-piperidinecarboxylate, 20 parts of potassium hydroxide, 160 parts of 2-propanol and 3 parts of water is stirred and refluxed for 36 hours. The reaction mixture is evaporated and water is added to the residue. The whole is acidified with a hydrochloric acid solution. Then it is basified with ammonium hydroxide and the free base is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is converted into the hydrochloride salt in 2-propanol. The salt is filtered off and dried, yielding 5-chloro-1,3-dihydro-1-(2-methyl-4-piperidinyl)-2H-benzimidazol-2-one hydrochloride.

Workup

  1. temperaturerefluxed for 36 hours
  2. customThe reaction mixture is evaporated
  3. additionwater is added to the residue
  4. extractionthe free base is extracted with trichloromethane
  5. customThe extract is dried
  6. filtrationfiltered
  7. customevaporated
  8. filtrationThe salt is filtered off
  9. customdried

Sources & evidence

ORD record
ord-cfd2bc0a939846de87e1a0892c0bfdc9
Source dataset
uspto-grants-1976_11
Patent number
US03989707

Reaction notes

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