m-Chloroperbenzoic acid → HCID 20548869, compound

HRID 2058967Notes

Reaction equation

HRID 2058967 reaction equation
[Cl:1][C:2]([Cl:14])([Cl:13])[CH2:3][O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]=[CH:9][CH2:8]1)=[O:6].ClC1C=CC=C(C(OO)=[O:23])C=1>C(Cl)Cl>[O:23]1[CH:10]2[CH:9]1[CH2:8][N:7]([C:5]([O:4][CH2:3][C:2]([Cl:1])([Cl:13])[Cl:14])=[O:6])[CH2:12][CH2:11]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 20548897HCID 20548897, compound

Product 1

HCID 20548869HCID 20548869, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

100 g (0.38 mol) of 1-(β,β,β-trichloroethoxycarbonyl)-1,2,5,6-tetrahydropyridine are dissolved in 1,200 ml of methylene chloride and the solution is treated with 157 g (0.77 mol) of 85% strength m-chloroperbenzoic acid in portions. The slightly exothermic reaction is kept at room temperature by means of a water bath. After the addition has ended (which takes about 2 hours), the reaction mixture, in which a white suspension forms, is stirred for a further 15 hours at room temperature. The m-chlorobenzoic acid which has precipitated is filtered off and the filtrate is washed with a saturated aqueous solution of sodium carbonate, then with aqueous iron-II sulphate solution, then with 0.1 N sodium hydroxide solution and finally with water, dried over sodium sulphate and evaporated under a water pump vacuum. The oil which remains is dissolved in 100 ml of benzene and the solution is filtered through a layer of silica gel. Elution with a benzene/ethyl acetate mixture (1:1) and evaporation of the solvent gives pure 3,4-epoxy-1-(β,β,β-trichloroethoxycarbonyl)-piperidine in the form of a slightly orange coloured oil.

Workup

  1. customThe slightly exothermic reaction
  2. customis kept at room temperature by means of a water bath
  3. additionAfter the addition
  4. custom(which takes about 2 hours)
  5. customThe m-chlorobenzoic acid which has precipitated
  6. filtrationis filtered off
  7. washthe filtrate is washed with a saturated aqueous solution of sodium carbonate
  8. dry with materialwith aqueous iron-II sulphate solution, then with 0.1 N sodium hydroxide solution and finally with water, dried over sodium sulphate
  9. customevaporated under a water pump vacuum
  10. dissolutionThe oil which remains is dissolved in 100 ml of benzene
  11. filtrationthe solution is filtered through a layer of silica gel
  12. washElution
  13. customwith a benzene/ethyl acetate mixture (1:1) and evaporation of the solvent

Sources & evidence

ORD record
ord-a9713c70e691408a8ac24f91221b5d03
Source dataset
uspto-grants-1982_03
Patent number
US04320137

Reaction notes

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