m-Chloroperbenzoic acid → HCID 67077756, compound

HRID 1959586Notes

Reaction equation

HRID 1959586 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[Cl:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([Cl:27])[C:18]=1[CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1>C(Cl)Cl>[Cl:12][C:13]1[CH:14]=[N+:15]([O-:6])[CH:16]=[C:17]([Cl:27])[C:18]=1[CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 44190364HCID 44190364, compound

Product 1

HCID 67077756HCID 67077756, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperoxybenzoic acid (mCPBA, 1.32 g, 7.66 mmol) was added to a stirred solution of 3,5-Dichloro-4-(tetrahydro-pyran-2-yloxymethyl)-pyridine (200 mg, 0.766 mmol) in DCM (5 mL). After stirring for 3 h at RT the solvent was removed in vacuo and the residue was partitioned between DCM (50 mL) and 2 N NaOH solution (50 mL). After extraction of the organic layer with water (50 mL) the organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The resulting title compound was used for the next reaction without purification. MS (m/z): 278.0 [M+H+].

Workup

  1. customwas removed in vacuo
  2. customthe residue was partitioned between DCM (50 mL) and 2 N NaOH solution (50 mL)
  3. extractionAfter extraction of the organic layer with water (50 mL) the organic layer
  4. dry with materialwas dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting title compound was used for the next reaction without purification

Sources & evidence

ORD record
ord-bca6432a41e04b1ab4b085f543be263d
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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