m-Chloroperbenzoic acid → HCID 86743681, compound

HRID 329752Notes

Reaction equation

HRID 329752 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[C:26]3[O:25][CH:24]([CH3:27])[C:23](=[O:28])[N:22]([CH3:29])[C:21]=3[CH:20]=[C:19]([Cl:30])[CH:18]=2)=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:39])C=1>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH+:14]([O-:39])[C:15]([C:17]2[C:26]3[O:25][CH:24]([CH3:27])[C:23](=[O:28])[N:22]([CH3:29])[C:21]=3[CH:20]=[C:19]([Cl:30])[CH:18]=2)=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14719846HCID 14719846, compound

Product 1

HCID 86743681HCID 86743681, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2.7 g of N-(1-benzyl-4-piperidyl)-6-chloro-3,4-dihydro-2,4-dimethyl-3-oxo-2H-1,4-benzoxazine-8-carboxamide in 150 ml of chloroform is added portionwise 2.7 g of metachloroperbenzoic acid under cooling and stirring. After 0.5 hour, ammonia gas is bubbled through the reaction solution under stirring and the precipitate is filtered off. The mother liquor is distilled off under reduced pressure followed by recrystallizing the residue from ethanolisopropyl ether to give N-(1-benzyl-4-piperidyl)-6-chloro-3,4-dihydro-2,4-dimethyl-3-oxo-2H-1,4-benzoxazine-8-carboxamide N-oxide.

Workup

  1. temperatureunder cooling
  2. customammonia gas is bubbled through the reaction solution
  3. stirringunder stirring
  4. filtrationthe precipitate is filtered off
  5. distillationThe mother liquor is distilled off under reduced pressure
  6. customby recrystallizing the residue from ethanolisopropyl ether

Sources & evidence

ORD record
ord-9f1aedced7b748c081ee67a620496c9f
Source dataset
uspto-grants-1990_01
Patent number
US04892872

Reaction notes

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