Hydrogen Peroxide → N-(1-cyclohexylmethylpiperid-4-yl)-2-methoxy-4-acetamido-5-chlorobenzamide N-oxide

HRID 261057Notes

Reaction equation

HRID 261057 reaction equation
[CH:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:29])[C:16]3[CH:21]=[C:20]([Cl:22])[C:19]([NH:23][C:24](=[O:26])[CH3:25])=[CH:18][C:17]=3[O:27][CH3:28])[CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:30]O>C(O)(=O)C>[CH:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH+:14]([O-:30])[C:15](=[O:29])[C:16]3[CH:21]=[C:20]([Cl:22])[C:19]([NH:23][C:24](=[O:26])[CH3:25])=[CH:18][C:17]=3[O:27][CH3:28])[CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 20395820N-(1-cyclohexylmethylpiperid-4-yl)-2-methoxy-4-acetamido-5-chlorobenzamide

Product 1

HCID 86736602N-(1-cyclohexylmethylpiperid-4-yl)-2-methoxy-4-acetamido-5-chlorobenzamide N-oxide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of N-(1-cyclohexylmethylpiperid-4-yl)-2-methoxy-4-acetamido-5-chlorobenzamide (10 g; 0.023 moles) in glacial acetic acid (50 ml) a 30% hydrogen peroxide solution (6 ml) was added. The mixture was heated for 8 hours at a temperature between 70° and 80° C. Afterwards the solvent was evaporated in vacuo, and N-(1-cyclohexylmethylpiperid-4-yl)-2-methoxy-4-acetamido-5-chlorobenzamide N-oxide was obtained as a viscous liquid. After recrystallisation from a mixture of acetone and diethyl ether, there was obtained 7.3 g of the N-oxide, melting at 206°-208° C.

Workup

  1. temperatureThe mixture was heated for 8 hours at a temperature between 70° and 80° C
  2. customAfterwards the solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-38d8b07a31f448b89723524deab9d91f
Source dataset
uspto-grants-1979_08
Patent number
US04163789

Reaction notes

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