m-Chloroperbenzoic acid → HCID 21327196, compound

HRID 614804Notes

Reaction equation

HRID 614804 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([O:10]O)=O)[CH:3]=1.[C:12]([N:15]1[CH2:20][CH2:19]C(C2C=CC=CC=2)=[CH:17][CH2:16]1)(=[O:14])[CH3:13]>C(Cl)Cl>[C:12]([N:15]1[CH2:20][CH2:19][C:8]2([O:10][CH:17]2[CH2:16]1)[C:4]1[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=1)(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 21327219HCID 21327219, compound

Product 1

HCID 21327196HCID 21327196, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.0 G. of 85% m-chloroperbenzoic acid was added portionwise to a solution of 5.8 g. of 1-acetyl-4-phenyl-1,2,5,6-tetrahydropyridine dissolved in 100 ml. of methylene chloride, the latter being cooled during the addition using an ice bath. The mixture was stirred 18 hours at room temperature, then washed with water, sodium bisulfite solution, sodium carbonate solution and, finally, again with water. After evaporation 4.8 g. of solid remained, which was recrystallised from ether to give 3.9 g. of the desired product which was found to have a melting point of 68°-71° C.

Workup

  1. washwashed with water, sodium bisulfite solution, sodium carbonate solution
  2. customAfter evaporation 4.8 g
  3. customwhich was recrystallised from ether
  4. customto give 3.9 g

Sources & evidence

ORD record
ord-b23e48870b3c45a2845771fbe29afe9e
Source dataset
uspto-grants-1979_03
Patent number
US04146629

Reaction notes

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