m-Chloroperbenzoic acid → HCID 13042966, compound

HRID 1435344Notes

Reaction equation

HRID 1435344 reaction equation
[CH3:1][S:2]([N:5]1[CH:10]=[CH:9][CH2:8][CH2:7][CH2:6]1)(=[O:4])=[O:3].ClC1C=C(C=CC=1)C(OO)=[O:16]>C(Cl)Cl>[CH3:1][S:2]([N:5]1[CH2:6][CH2:7][CH:8]2[CH:9]([O:16]2)[CH2:10]1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 69080582HCID 69080582, compound

Product 1

HCID 13042966HCID 13042966, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of N-methanesulfony-1,2,3,4-tetrahydropyridine (2.18 g, 13.52 mmol, Example 302) in methylene chloride (30 mL) at 0° C., meta-chloroperoxybenzoic acid (3.94 g, 77%, 17.5 mmol, Aldrich) in 20 mL of methylene chloride was added and the mixture was stirred for 30 minutes. An additional 600 mg of meta-chloroperoxybenzoic acid was added and the mixture was stirred for 6 hours. The reaction was quenched with 30% sodium thiosulfate solution and the mixture was extracted with methylene chloride. The extracts were combined, washed with 5% sodium carbonate and dried with MgSO4. The solvent was removed to give the desired product as a white solid. 2.40 g, 100%. The compound was used directly for the next step.

Workup

  1. stirringthe mixture was stirred for 6 hours
  2. customThe reaction was quenched with 30% sodium thiosulfate solution
  3. extractionthe mixture was extracted with methylene chloride
  4. washwashed with 5% sodium carbonate
  5. dry with materialdried with MgSO4
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-f636adbe8e294e9bb5314a651b3541c3
Source dataset
uspto-grants-2009_11
Patent number
US07615634B2

Reaction notes

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