Sodium Chloride → HCID 69700183, compound

HRID 352735Notes

Reaction equation

HRID 352735 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:25](=[O:38])[C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)=[CH:28][CH:27]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].S([O-])([O-])(=O)=S.[Na+].[Na+].[Na+].[Cl-]>ClCCl>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:25]([C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N+:33]=3[O-:9])=[CH:28][CH:27]=2)=[O:38])[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 22709582HCID 22709582, compound

Product 1

HCID 69700183HCID 69700183, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At −10° C., metachloroperbenzoic acid (789 mg) was added to a solution of 1-tert-butoxycarbonyl-4-[4-(2-pyridyl)benzoyl]piperazine (517 mg) in dichloromethane (dichloromethane: 8 ml). The resulting mixture was stirred for 24 hours, followed by dilution with dichloromethane. A small amount of an aqueous sodium thiosulfate solution and a saturated aqueous NaCl solution were added to the dilute solution. The organic layer so separated was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous NaCl solution and then dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column (dichloromethane:methanol=20:1), whereby the title compound (415 mg, 77%) was obtained.

Workup

  1. customThe organic layer so separated
  2. washwas washed with a saturated aqueous solution of sodium bicarbonate
  3. dry with materiala saturated aqueous NaCl solution and then dried over anhydrous sodium sulfate
  4. customThe residue obtained
  5. distillationby distilling off the solvent under reduced pressure
  6. customwas purified by chromatography on a silica gel column (dichloromethane:methanol=20:1), whereby the title compound (415 mg, 77%)
  7. customwas obtained

Sources & evidence

ORD record
ord-fcfc2bb6eb894404821dd661bccb7396
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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