Hydrochloric Acid → (R)-2-{3-[1-(acenaphthen-1-yl)piperidin-4-yl]-2,3-dihydro-2-oxo-benzoimidazol-1-yl}acetic Acid

HRID 1675386Notes

Reaction equation

HRID 1675386 reaction equation
[C@H:1]1([N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[N:21]([CH2:28][C:29]([O:31]CC)=[O:30])[C:20]3=[O:34])[CH2:15][CH2:14]2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[CH2:2]1.[OH-].[Na+].O.Cl>C(O)C>[C@H:1]1([N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[N:21]([CH2:28][C:29]([OH:31])=[O:30])[C:20]3=[O:34])[CH2:15][CH2:14]2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 24901038(R)-Ethyl 2-(3-(1-(1,2-dihydroacenaphthylen-1-yl)piperidin-4-yl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)acetate

Product 1

HCID 24901039(R)-2-{3-[1-(acenaphthen-1-yl)piperidin-4-yl]-2,3-dihydro-2-oxo-benzoimidazol-1-yl}acetic AcidYield 96.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl (R)-2-{3-[1-(acenaphthen-1-yl)piperidin-4-yl]-2,3-dihydro-2-oxo-benzoimidazol-1-yl}acetate (2.6 g, 5.8 mmol) was dissolved in ethanol (10 ml), 2N-aqueous sodium hydroxide solution (10 ml) was added and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into water, 1N-hydrochloric acid was added for neutralization, and the mixture was extracted with chloroform. The extract was washed with water and saturated brine, dried over magnesium sulfate, and concentrated. The obtained solid was washed with ethyl acetate to give the title compound (2.4 g) as pale-yellow crystals.

Workup

  1. additionwas added for neutralization
  2. extractionthe mixture was extracted with chloroform
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. washThe obtained solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-a240a4be0a3e434d9d90280b182a7f5e
Source dataset
uspto-grants-2011_08
Patent number
US08003669B2

Reaction notes

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