Hydrogen Peroxide → HCID 178483450, compound

HRID 2057293Notes

Reaction equation

HRID 2057293 reaction equation
OO.NC(N)=[O:5].C1(=O)OC(=O)C2=CC=CC=C12.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26](=[O:44])[N:27]([C@H:29]2[CH2:34][CH2:33][C@H:32]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][N:41]([CH3:43])[CH3:42])[CH2:31][CH2:30]2)[CH3:28])=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([O:25][C:26](=[O:44])[N+:27]([O-:5])([C@H:29]2[CH2:34][CH2:33][C@H:32]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][N:41]([CH3:42])[CH3:43])[CH2:31][CH2:30]2)[CH3:28])=[CH:23][CH:24]=1

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 1176UreaHCID 6811Phthalic AnhydrideHCID 11430Potassium CarbonateHCID 178483449HCID 178483449, compound

Product 1

HCID 178483450HCID 178483450, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 1.39 g (4.4 mmol, 2.2 eq) Hydrogen peroxide.Urea adduct in CH2Cl2, 338.5 mg (2.2 mmol, 1.1 eq) phthalic anhydride were added and stirred for 15 min at RT. 800 mg (2.01 mmol) trans-[4-(5-Dimethylamino-pentyloxy)-cyclohexyl]-methyl-carbamic acid 4-chloro-phenyl ester in CH2Cl2 was added and the mixture was stirred at RT for 2 h. 5% aqueous K2CO3 solution was added and the inorganic-phase was extracted with CH2Cl2. The organic phases were washed with water and brine and dried over MgSO4. Column chromatography yielded 525 mg (63%) trans-[4-(5-Dimethylamino-pentyloxy)-cyclohexyl]-methyl-carbamic acid 4-chloro-phenyl ester N-oxide as colourless oil, MS: 413 (MH+, 1Cl).

Workup

  1. stirringthe mixture was stirred at RT for 2 h
  2. extractionthe inorganic-phase was extracted with CH2Cl2
  3. washThe organic phases were washed with water and brine
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-2d1eac1e785944808741b475c798ec1f
Source dataset
uspto-grants-2008_02
Patent number
US07335687B2

Reaction notes

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