m-Chloroperbenzoic acid → HCID 22351550, compound

HRID 2418461Notes

Reaction equation

HRID 2418461 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:7][CH:6]([N:8]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=[O:15])[CH2:5][C:4]([CH3:17])([CH3:16])[NH:3]1.ClC1C=CC=C(C(OO)=[O:27])C=1>C(Cl)(Cl)Cl>[OH:27][N:3]1[C:4]([CH3:17])([CH3:16])[CH2:5][CH:6]([N:8]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=[O:15])[CH2:7][C:2]1([CH3:18])[CH3:1]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 185514351-(2,2,6,6-Tetramethylpiperidin-4-yl)azepan-2-one

Product 1

HCID 22351550HCID 22351550, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 25.4 g (0.1 mole) of the lactam compound prepared in Example 1 in 200 ml of chloroform is added portionwise 38 g (0.22 mole) of m-chloroperbenzoic acid over a one-hour period. The reaction mixture is stirred for an eighteen-hour period at ambient temperature. The mixture is then filtered to remove the m-chlorobenzoic acid formed. The filtrate is washed successively with 1N sulfuric acid, with water and with 10% aqueous sodium bicarbonate and then dried. The solvent is removed in vacuo and the residue recrystallized from tolueneheptane to give the above-named compound as an orange solid melting at 158°-164° C.

Workup

  1. filtrationThe mixture is then filtered
  2. customto remove the m-chlorobenzoic acid
  3. customformed
  4. washThe filtrate is washed successively with 1N sulfuric acid, with water and with 10% aqueous sodium bicarbonate
  5. customdried
  6. customThe solvent is removed in vacuo
  7. customthe residue recrystallized from tolueneheptane

Sources & evidence

ORD record
ord-4b6a715728784e16b9de9360b5d1290a
Source dataset
uspto-grants-1984_09
Patent number
US04472547

Reaction notes

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