m-Chloroperbenzoic acid → HCID 86596635, compound

HRID 131106Notes

Reaction equation

HRID 131106 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][O:10][N:11]=[C:12]([Cl:22])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:31])C=1>C(Cl)(Cl)Cl>[OH2:10].[OH2:31].[O-:31][N+:1]1([CH2:7][CH2:8][CH2:9][O:10][N:11]=[C:12]([Cl:22])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54010937HCID 54010937, compound

Product 1

HCID 86596635HCID 86596635, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of 1.0 g (3.0 mmol) of N-[3-(1-piperidinyl)propoxy]-3-nitro-benzimidoyl-chloride in 5 ml of chloroform a solution of 0.725 g (4.2 mmol) of m-chloroperbenzoic acid in 6 ml of chloroform is added. The reaction mixture is stirred for 6 hours at 25° C., then evaporated. To the residue 12 ml of 2 M potassium carbonate solution is added, and extracted 5 times with 20 ml of chloroform. The combined extracts are dried over magnesium sulfate, filtered and evaporated. The product is dissolved in ethanol; the solution is treated with charcoal then evaporated. The obtained material is triturated with ethylacetate, filtered and dried.

Workup

  1. customevaporated
  2. additionTo the residue 12 ml of 2 M potassium carbonate solution is added
  3. extractionextracted 5 times with 20 ml of chloroform
  4. dry with materialThe combined extracts are dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. dissolutionThe product is dissolved in ethanol
  8. additionthe solution is treated with charcoal
  9. customthen evaporated
  10. customThe obtained material is triturated with ethylacetate
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-cb4f892445d7462ea80fd9fe579d0dd8
Source dataset
uspto-grants-2008_06
Patent number
US07384936B2

Reaction notes

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