m-Chloroperbenzoic acid → HCID 68592779, compound

HRID 1864494Notes

Reaction equation

HRID 1864494 reaction equation
C(OC([N:8]1[CH2:13][C@H:12]([CH3:14])[N:11](CCC(=O)C)[C@H:10]([CH3:20])[CH2:9]1)=O)(C)(C)C.[Cl:21]C1C=CC=C(C(OO)=[O:29])C=1>C(Cl)(Cl)Cl>[ClH:21].[CH3:14][C@H:12]1[CH2:13][NH:8][CH2:9][C@@H:10]([CH3:20])[N:11]1[OH:29]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59710226HCID 59710226, compound

Product 1

HCID 68592779HCID 68592779, compoundYield 8.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Cis-3,5-Dimethyl-4-(3-oxo-butyl)-piperazine-1-carboxylic acid tert-butyl ester (1.00 g) in chloroform (40 mL) was treated with m-chloroperbenzoic acid (77%, 0.97 g ) at 0° C. The solution was allowed to warm to room temperature and stirred overnight. The reaction mixture was then cooled to 0° C., filtered to remove precipitates, washed with saturated aqueous sodium bicarbonate, filtered through a plug of silica gel and concentrated. The residue was taken up in a 1:1 mixture of DCM and MeOH and treated with an excess of 4.0 M HCl/dioxane. The reaction mixture was stirred overnight and then purified by column chromatography (0 to 10% MeOH:DCM) to yield 50 mg of the title compound. ESMS (0.41 minutes, (M+1) 131.13, Method E).

Workup

  1. temperatureThe reaction mixture was then cooled to 0° C.
  2. filtrationfiltered
  3. customto remove
  4. customprecipitates
  5. washwashed with saturated aqueous sodium bicarbonate
  6. filtrationfiltered through a plug of silica gel
  7. concentrationconcentrated
  8. additionThe residue was taken up in a 1:1 mixture of DCM and MeOH
  9. additiontreated with an excess of 4.0 M HCl/dioxane
  10. stirringThe reaction mixture was stirred overnight
  11. custompurified by column chromatography (0 to 10% MeOH:DCM)

Sources & evidence

ORD record
ord-63c0a4b3f56e48f2bd91d217da33c254
Source dataset
uspto-grants-2009_12
Patent number
US07625909B2

Reaction notes

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