1,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one → HCID 69198199, compound

HRID 132580Notes

Reaction equation

HRID 132580 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.[N+:17]([C:20]1[CH:30]=[CH:29][CH:28]=[CH:27][C:21]=1[O:22][CH2:23][CH:24]1[CH2:26][O:25]1)([O-])=O.C([O-])=O.[NH4+]>CCO.[Pd]>[NH2:17][C:20]1[CH:30]=[CH:29][CH:28]=[CH:27][C:21]=1[O:22][CH2:23][CH:24]([OH:25])[CH2:26][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

6

Reactant 3

HCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 2199222-[(2-nitrophenoxy)methyl]oxiraneHCID 2723923Ammonium formate

Product 1

HCID 69198199HCID 69198199, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-(4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one (0.434 g, 2.0 mmol), 2-[(2-nitrophenoxy)methyl]oxirane (0.390 g g, 2.0 mmol) in EtOH (95%, 3 ml, was stirred for 2 hours at 78° C. The reaction mixture was cooled and Pd—C (5%, 0.20 g) was added. Then ammonium formiate (1.26 g, 20 mmol) was added in portions during 5 min. After 90 min the reaction mixture was filtered through Celite, concentrated, partioned between dichloromethane and ammonium hydoxide (25%) and purified on silica (dichloromethane-methanol, 12:1, containing 1% of NH4OH (25%)) to give the subtitle compound.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationAfter 90 min the reaction mixture was filtered through Celite
  3. concentrationconcentrated
  4. custompurified on silica (dichloromethane-methanol, 12:1, containing 1% of NH4OH (25%))

Sources & evidence

ORD record
ord-33f5da474b544f13a48052d65c1ee393
Source dataset
uspto-grants-2008_06
Patent number
US07388020B2

Reaction notes

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