Hydrochloric Acid → 1H-Benzimidazole, 5,6-difluoro-2-[[2-(1-piperazinyl)ethyl]thio]-

HRID 1354253Notes

Reaction equation

HRID 1354253 reaction equation
[F:1][C:2]1[C:21]([F:22])=[CH:20][C:5]2[N:6]=[C:7]([S:9][CH2:10][CH2:11][N:12]3[CH2:17][CH2:16][N:15](C=O)[CH2:14][CH2:13]3)[NH:8][C:4]=2[CH:3]=1.Cl>CO>[F:1][C:2]1[C:21]([F:22])=[CH:20][C:5]2[N:6]=[C:7]([S:9][CH2:10][CH2:11][N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[NH:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 231161611-[2-(5,6-Difluorobenzimidazol-2-ylthio)ethyl]-4-formylpiperazine

Product 1

HCID 115222491H-Benzimidazole, 5,6-difluoro-2-[[2-(1-piperazinyl)ethyl]thio]-Yield 90.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[2-(5,6-Difluorobenzimidazol-2-ylthio)ethyl]-4-formylpiperazine (1.70 g, 5.2 mmol) was dissolved in methanol (20 mL), and 12N hydrochloric acid (2 mL) was added to the solution, followed by stirring for 18 hours at room temperature. The reaction mixture was concentrated under reduced pressure, and saturated ammonia-methanol was added thereto, followed by stirring for five minutes at room temperature. The solvent was removed under reduced pressure, and the residue was purified through silica gel column chromatography (chloroform: saturated ammonia-methanol=100:3), to thereby yield 1-[2-(5,6-difluorobenzimidazol-2-ylthio)ethyl]piperazine (1.40 g, yield 90%) as a brown oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and saturated ammonia-methanol
  2. additionwas added
  3. stirringby stirring for five minutes at room temperature
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified through silica gel column chromatography (chloroform: saturated ammonia-methanol=100:3)

Sources & evidence

ORD record
ord-81c3da7ab46f46ccbc46531ceb38700a
Source dataset
uspto-grants-2007_05
Patent number
US07223764B2

Reaction notes

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