Hydrochloric Acid → 5-Fluoro-1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one

HRID 1295765Notes

Reaction equation

HRID 1295765 reaction equation
C(OC([N:6]1[CH2:11][CH2:10][CH:9]([N:12]2[C:16]3[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:15]=3[NH:14][C:13]2=[O:22])[CH2:8][CH2:7]1)=O)C.[OH-].[Na+].Cl.C(=O)([O-])[O-].[Na+].[Na+]>>[F:21][C:19]1[CH:18]=[CH:17][C:16]2[N:12]([CH:9]3[CH2:8][CH2:7][NH:6][CH2:11][CH2:10]3)[C:13](=[O:22])[NH:14][C:15]=2[CH:20]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 137921864-(5-Fluoro-2-oxo-2,3-dihydro-benzoimidazol-1-yl)-piperidine-1-carboxylic acid ethyl ester

Product 1

HCID 137921045-Fluoro-1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-oneYield 73%

Procedure

4-(5-Fluoro-2-oxo-2,3-dihydro-benzoimidazol-1-yl)-piperidine-1-carboxylic acid ethyl ester was refluxed with 10% sodium hydroxide (2 mL) for 4 h. The reaction was allowed to cool to room temperature and acidified with concentrated hydrochloric acid. The acidified reaction mixture was adjusted to pH 10 with the slow addition of sodium carbonate. The pink solid that formed was collected by filtration and vacuum dried to give 5-Fluoro-1-piperidin-4-yl-1,3-dihydro-benzoimidazol-2-one (29.4 mg, 73%).

Workup

  1. customThe acidified reaction mixture
  2. customThe pink solid that formed
  3. filtrationwas collected by filtration and vacuum
  4. customdried

Sources & evidence

ORD record
ord-152261f4a42a4662b046b63a563cc65e
Source dataset
uspto-grants-2007_07
Patent number
US07244744B2

Reaction notes

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