HCID 68513291, compound → HCID 58852308, compound

HRID 1716578Notes

Reaction equation

HRID 1716578 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][C:21]([CH3:23])=[CH:22][C:17]=3[N:16]=[C:15]2[C:24](=[O:26])[CH3:25])[CH2:10][CH2:9]1)=O)(C)(C)C>FC(F)(F)C(O)=O.C(Cl)Cl>[CH3:23][C:21]1[CH:20]=[CH:19][C:18]2[N:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[C:15]([C:24](=[O:26])[CH3:25])=[N:16][C:17]=2[CH:22]=1

Participants

4

Reactant 1

HCID 68513291HCID 68513291, compound

Product 1

HCID 58852308HCID 58852308, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

4-(2-acetyl-5-methyl-benzoimidazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (107 mg, 0.30 mmol) was dissolved in a mixture of trifluoroacetic acid (2 mL) and CH2Cl2 (2 mL) at rt and stirred for 1 hour. The mixture was concentrated under reduced pressure and the residue was partitioned between dilute aqueous K2CO3 solution (20 mL) and CH2Cl2 (20 mL). The organic layer was separated, and the aqueous layer was extracted with CH2Cl2 (2×15 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure to give 1-(5-methyl-1-piperidin-4-yl-1H-benzoimidazol-2-yl)-ethanone as an oil (77 mg, 0.30 mmol, 100%) that was used without further purification or characterization.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between dilute aqueous K2CO3 solution (20 mL) and CH2Cl2 (20 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (2×15 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-db18570768d94ff4b8c81fc86864ddb6
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

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