Hydrogen Bromide → HCID 14012880, compound

HRID 1904833Notes

Reaction equation

HRID 1904833 reaction equation
Cl.Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:15]3[CH:16]=[CH:17][C:18]([O:20]C)=[CH:19][C:14]=3[N:13]=[C:12]2[CH2:22][CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[CH:6][CH:5]=1.Br>O>[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][N:11]2[C:15]3[CH:16]=[CH:17][C:18]([OH:20])=[CH:19][C:14]=3[N:13]=[C:12]2[CH2:22][CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 86741815HCID 86741815, compound

Product 1

HCID 14012880HCID 14012880, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 22.3 parts of 1-[(4-fluorophenyl)methyl]-5-methoxy-2-(4-piperidinylmethyl)-1H-benzimidazole dihydrochloride.monohydrate in 75 parts of a hydrobromic acid solution 48% in water was stirred and refluxed for 18 hours. The whole was slightly cooled and evaporated. The residue was dissolved in water. The solution was treated with an ammonium hydroxide solution. The product was extracted three times with trichloromethane. The combined organic layers were washed with water, dried, filtered and evaporated, yielding 15.7 parts (92%) of 1-[(4-fluorophenyl)methyl]-2-(4-piperidinylmethyl)-1H-benzimidazol-5-ol; mp. 210° C. (78).

Workup

  1. temperaturerefluxed for 18 hours
  2. temperatureThe whole was slightly cooled
  3. customevaporated
  4. dissolutionThe residue was dissolved in water
  5. additionThe solution was treated with an ammonium hydroxide solution
  6. extractionThe product was extracted three times with trichloromethane
  7. washThe combined organic layers were washed with water
  8. customdried
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-91a0d0e45d494ae69a7c4da969b20143
Source dataset
uspto-grants-1989_06
Patent number
US04839374

Reaction notes

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