Hydrochloric Acid → 6-Fluoro-2-{[2-(piperazin-1-yl)ethyl]sulfanyl}-1H-benzimidazole

HRID 1354261Notes

Reaction equation

HRID 1354261 reaction equation
[F:1][C:2]1[CH:21]=[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[CH:21]=[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 231161581-[2-(5-Fluorobenzimidazol-2-ylthio)ethyl]-4-formylpiperazine

Product 1

HCID 231161566-Fluoro-2-{[2-(piperazin-1-yl)ethyl]sulfanyl}-1H-benzimidazoleYield 81.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[2-(5-Fluorobenzimidazol-2-ylthio)ethyl]-4-formylpiperazine (1.80 g, 5.8 mmol) was dissolved in methanol (20 mL), 12N hydrochloric acid (2 mL) was added thereto, 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-fluorobenzimidazol-2-ylthio)ethyl]piperazine (1.33 g, yield 81%) 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-1a3fe4954d1548029244b48e0b0733ab
Source dataset
uspto-grants-2007_05
Patent number
US07223764B2

Reaction notes

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