Methyl morpholine oxide → 5-nitro-2-(4-oxocyclohexylamino)-N-(1,3-benzodioxol-5-ylmethyl)benzamide

HRID 1934646Notes

Reaction equation

HRID 1934646 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][C:10]=2[C:11]([NH:13][CH2:14][C:15]2[CH:23]=[CH:22][C:18]3[O:19][CH2:20][O:21][C:17]=3[CH:16]=2)=[O:12])[CH2:4][CH2:3]1.C[N+]1([O-])CCOCC1>ClCCl.C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[N+:28]([C:25]1[CH:26]=[CH:27][C:9]([NH:8][CH:5]2[CH2:6][CH2:7][C:2](=[O:1])[CH2:3][CH2:4]2)=[C:10]([CH:24]=1)[C:11]([NH:13][CH2:14][C:15]1[CH:23]=[CH:22][C:18]2[O:19][CH2:20][O:21][C:17]=2[CH:16]=1)=[O:12])([O-:30])=[O:29]

Participants

6

Reactant 2

HCID 82029Methyl morpholine oxideHCID 178522768HCID 178522768, compound

Product 1

HCID 224676195-nitro-2-(4-oxocyclohexylamino)-N-(1,3-benzodioxol-5-ylmethyl)benzamideYield 92.5%

Reagents, catalysts & solvents 3

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(trans-4-hydroxycyclohexylamino)-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide (100 mg) in dichloromethane (3 mL) and acetonitrile (0.4 mL) were added tetrapropylammonium perruthenate (4.25 mg), 4-methylmorpholine N-oxide (42.5 mg) and molecular sieves (4 Å, 0.2 g). The resulting mixture was stirred for 2 hours at ambient temperature. The mixture was subjected to a silica gel chromatography eluting with ethyl acetate to give 5-nitro-2-(4-oxocyclohexylamino)-N-(1,3-benzodioxol-5-ylmethyl)benzamide (92 mg) as a solid substance.

Workup

  1. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-5b10d0be1e1c4e75a138fc36ed7506e3
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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