Sodium Hydroxide → 1-[2-(4-Fluoro-1H-benzoimidazol-2-yl)-ethyl]-piperidine-4-carboxylic acid

HRID 456592Notes

Reaction equation

HRID 456592 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][C:14]2[NH:18][C:17]3[CH:19]=[CH:20][CH:21]=[C:22]([F:23])[C:16]=3[N:15]=2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>C(O)C>[F:23][C:22]1[C:16]2[N:15]=[C:14]([CH2:13][CH2:12][N:9]3[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]3)[NH:18][C:17]=2[CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 695222001-[2-(4-Fluoro-1H-benzoimidazol-2-yl)-ethyl]-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 179812241-[2-(4-Fluoro-1H-benzoimidazol-2-yl)-ethyl]-piperidine-4-carboxylic acidYield 54.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (b) (2.0 g, 6.3 mmol), 1M aqueous sodium hydroxide solution (1.2 ml, 1.2 mmol) in ethanol (40 ml) was stirred at room temperature for 3 hours. After concentration, the residue was diluted with water and acidified with a saturated solution of potassium hydrogenosulfate to pH 5. The precipitated solid was filtered, washed with water and dried under vacuum to afford a foam (1.0 g, 54%).

Workup

  1. concentrationAfter concentration
  2. additionthe residue was diluted with water
  3. filtrationThe precipitated solid was filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-19ae984c130b4308b2975f6746a8adc5
Source dataset
uspto-grants-2007_03
Patent number
US07186730B2

Reaction notes

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