m-Chloroperbenzoic acid → HCID 19099425, compound

HRID 1975369Notes

Reaction equation

HRID 1975369 reaction equation
[CH2:1]([S:3]([CH2:5][C:6]([NH:8][C:9]1[CH:31]=[CH:30][C:12]([C:13]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[CH2:17][CH2:16]2)=[O:14])=[CH:11][CH:10]=1)=[O:7])=[O:4])[CH3:2].ClC1C=CC=C(C(OO)=[O:40])C=1>CN(C)C=O.O1CCCC1>[CH2:1]([S:3]([CH2:5][C:6]([NH:8][C:9]1[CH:31]=[CH:30][C:12]([C:13]([N:15]2[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][C:23]3[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=3)[CH2:19][CH2:20]2)=[O:14])=[CH:11][CH:10]=1)=[O:7])(=[O:40])=[O:4])[CH3:2]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19099483HCID 19099483, compound

Product 1

HCID 19099425HCID 19099425, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.4 g of 1-[4-(N-ethylsulfinylacetylamino)benzoyl]-4-[2-(4-chlorophenyl)ethyl]piperazine (Example 46) are dissolved in 50 ml of dimethylformamide, and a solution of 3-chloroperbenzoic acid (85%) in 30 ml of tetrahydrofuran is added dropwise at RT. The clear solution is stirred overnight at RT. The mixture is concentrated by evaporation, the residue is dissolved in water and the solution is rendered neutral, extracted with dichloromethane, chromatographed over silica gel and crystallised from ether/petroleum ether/alcohol, yielding 1-[4-(N-ethylsulfonylacetylamino)benzoyl]-4-[2-(4-chlorophenyl)ethyl]piperazine having a melting point of 135°-136°.

Workup

  1. concentrationThe mixture is concentrated by evaporation
  2. dissolutionthe residue is dissolved in water
  3. extractionextracted with dichloromethane
  4. customchromatographed over silica gel
  5. customcrystallised from ether/petroleum ether/alcohol

Sources & evidence

ORD record
ord-7c3714839dca4cd2b966343a0732fe31
Source dataset
uspto-grants-1994_02
Patent number
US05286728

Reaction notes

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