Lithium Hydroxide → 1-(1-(4-chlorobenzyl)-1H-benzo[d]imidazole-2-carbonyl)piperidine-4-carboxylic acid

HRID 83652Notes

Reaction equation

HRID 83652 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]([O:26]CC)=[O:25])[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1.[OH-].[Li+]>C1COCC1.O.C(OCC)C>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C:16]([N:18]2[CH2:19][CH2:20][CH:21]([C:24]([OH:26])=[O:25])[CH2:22][CH2:23]2)=[O:17])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 68379871ethyl 1-(1-(4-chlorobenzyl)-1H-benzo[d]imidazole-2-carbonyl)piperidine-4-carboxylate

Product 1

HCID 683800451-(1-(4-chlorobenzyl)-1H-benzo[d]imidazole-2-carbonyl)piperidine-4-carboxylic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

ethyl 1-(1-(4-chlorobenzyl)-1H-benzo[d]imidazole-2-carbonyl)piperidine-4-carboxylate (60 mg, 0.141 mmol) and lithium hydroxide, H2O (23.65 mg, 0.564 mmol) were dissolved in THF (Ratio: 1.000, Volume: 0.25 ml) and Water (Ratio: 2, Volume: 0.500 ml). The reaction was stirred for two hours before it was diluted with water and diethyl ether. The aqueous phase was washed with diethyl ether twice. It was then acidified to pH ˜2 and extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated to obtain crude acid. No further purification was performed. (Yield: 54 mg, white solid). 1H-NMR (400 MHz, DMSO-d6) 12.28, 7.65, 7.36-7.18, 5.51, 4.36-4.27, 3.91-3.82, 3.12, 2.96, 1.92-1.83, 1.74-1.63, 1.50-1.17

Workup

  1. washThe aqueous phase was washed with diethyl ether twice
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto obtain crude acid
  8. customNo further purification

Sources & evidence

ORD record
ord-2e20d65f52a243548ebafd97aed953f4
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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