Ammonium Hydroxide → HCID 69197184, compound

HRID 132578Notes

Reaction equation

HRID 132578 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[NH:9][C:8]2=[O:16])[CH2:3][CH2:2]1.FC(F)(F)C([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[O:28][CH2:29][C:30]1([CH3:33])[CH2:32][O:31]1)=O.[OH-].[NH4+]>CCO>[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[O:28][CH2:29][C:30]([OH:31])([CH3:33])[CH2:32][N:1]1[CH2:2][CH2:3][CH:4]([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[NH:9][C:8]2=[O:16])[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 86760690HCID 86760690, compound

Product 1

HCID 69197184HCID 69197184, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one (1.10 g, 5.05 mmol), 2,2,2-trifluoro-N-{2-[(2-methyl-2-oxiranyl)methoxy]phenyl}acetamide (1.39 g, 5.05 mmol) in EtOH (95%, 20 ml,) was stirred for 2 h at 78° C. Ammonium hydroxide (25%, 7.5 ml) was added to the reaction mixture and heating was continued for additional 5 h. After standing over night at room temperature the reaction mixture was concentrated and the residue was purified on silica (dichloromethane-methanol, 12:1, containing 1% of NH4OH (25%)) to give the subtitle compound (1.54 g).

Workup

  1. temperatureheating
  2. waitAfter standing over night at room temperature
  3. concentrationthe reaction mixture was concentrated
  4. customthe residue was purified on silica (dichloromethane-methanol, 12:1, containing 1% of NH4OH (25%))

Sources & evidence

ORD record
ord-1d125c3c23c8406d8b7ddb71015dba78
Source dataset
uspto-grants-2008_06
Patent number
US07388020B2

Reaction notes

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