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

HRID 1870615Notes

Reaction equation

HRID 1870615 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.[NH4+].[Cl-].[OH-].C([O-])([O-])=O.[Na+].[Na+]>[OH-].[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

6

Reactant 4

HCID 961HydroxideHCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 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)-one

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

A suspension of 1-ethoxycarbonyl-4-(5-fluoro-2-oxo-1-benzimidazolinyl)piperidine (5.22 g, 17 mmol.) in 2 N NaOH (55 mL) was refluxed for twelve hours. The clear amber solution was cooled to room temp. and solid NH4Cl (5.9 g, 110 mmol.) was added to neutralized the hydroxide. After addition of aq. Na2CO3 and 5 N NaOH (2 mL), the product was extracted into chloroform. The extract was dried (Na2SO4) and filtered through a pad of charcoal and then evaporated to give 4-(5-fluoro-2-oxo-1-benzimidazolinyl)piperidine as a pale yellow viscous oil.

Workup

  1. temperaturewas refluxed for twelve hours
  2. temperatureThe clear amber solution was cooled to room temp.
  3. extractionthe product was extracted into chloroform
  4. dry with materialThe extract was dried (Na2SO4)
  5. filtrationfiltered through a pad of charcoal
  6. customevaporated

Sources & evidence

ORD record
ord-d45bd9a535514a40a31fedc668b03c53
Source dataset
uspto-grants-2000_08
Patent number
US06096763

Reaction notes

Loading…