Isopropanol → HCID 13792109, compound

HRID 1729792Notes

Reaction equation

HRID 1729792 reaction equation
[O:1]=[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][N:10](C(OCC)=O)[CH2:9][CH2:8]2)[C:5]2[CH:18]=[CH:19][C:20]([C:22]([F:25])([F:24])[F:23])=[CH:21][C:4]=2[NH:3]1.[OH-].[K+].CC(O)C>O>[NH:10]1[CH2:11][CH2:12][CH:7]([N:6]2[C:5]3[CH:18]=[CH:19][C:20]([C:22]([F:24])([F:23])[F:25])=[CH:21][C:4]=3[NH:3][C:2]2=[O:1])[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 13792185HCID 13792185, compound

Product 1

HCID 13792109HCID 13792109, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 26 parts of ethyl 4-[1,3-dihydro-2-oxo-5-(trifluoromethyl)-2H-benzimidazol-1-yl]-1-piperidinecarboxylate, 30 parts of potassium hydroxide, 176 parts of 2-propanol and 4 parts of water is stirred and refluxed for 20 hours. The reaction mixture is evaporated. The residue is dissolved in water, acidified with a concentrated hydrochloric acid solution, while cooling, and alkalized with a concentrated ammonium hydroxide solution. The product is extracted with trichloromethane. The extract is washed with water, dried, filtered and evaporated. The residue is crystallized from a mixture of 2,2'-oxybispropane and 2-propanol. The product is filtered off and dried, yielding 1,3-dihydro-1-(4-piperidinyl)-5-(trifluoromethyl)-2H-benzimidazol-2-one; mp. 198° C.

Workup

  1. temperaturerefluxed for 20 hours
  2. customThe reaction mixture is evaporated
  3. dissolutionThe residue is dissolved in water
  4. temperaturewhile cooling
  5. extractionThe product is extracted with trichloromethane
  6. washThe extract is washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue is crystallized from a mixture of 2,2'-oxybispropane and 2-propanol
  11. filtrationThe product is filtered off
  12. customdried

Sources & evidence

ORD record
ord-f677014f3fdc490c8f2a13a30be01f14
Source dataset
uspto-grants-1976_11
Patent number
US03989707

Reaction notes

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