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Methyl morpholine oxide → 1-[1-(2,4-Dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazol-7-yl]propan-1-one

HRID 1399010
Notes
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Reaction equation

HRID 1399010 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:15]2=[N:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]([OH:26])[CH2:24][CH3:25])[C:18]=3[N:14]2[CH2:13][CH2:12][CH2:11][CH2:10]1.C[N+]1([O-])CCOCC1>[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC.ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:15]2=[N:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23](=[O:26])[CH2:24][CH3:25])[C:18]=3[N:14]2[CH2:13][CH2:12][CH2:11][CH2:10]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 57786122HCID 57786122, compound

Product 1

HCID 577863481-[1-(2,4-Dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazol-7-yl]propan-1-one

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-[1-(2,4-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazol-7-yl]propan-1-ol (160 mg, 0.409 mmol), tetra-n-propylammonium perruthenate (144 mg, 0.409 mmol), 4-methylmorpholine N-oxide (47.9 mg, 0.409 mmol) and dichloromethane (2.0 mL) was stirred at room temperature for 32 hr. The precipitate was removed by filtration, and the mother solution was diluted with aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound as a colorless amorphous (11.0 mg, 0.0283 mmol, 7%).

Workup

  1. customThe precipitate was removed by filtration
  2. additionthe mother solution was diluted with aqueous sodium hydrogen carbonate
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture
  9. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-90b75c4646f243bab03c9c88cdd4801d
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08901141B2

Reaction notes

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