m-Chloroperbenzoic acid → (E)-1-[4-(2-Methyl-1-oxido-quinolin-1-ium-4-yl)piperazin-1-yl]pent-2-en-1-one

HRID 333973Notes

Reaction equation

HRID 333973 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18](=[O:23])/[CH:19]=[CH:20]/[CH2:21][CH3:22])[CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.ClC1C=CC=C(C(OO)=[O:32])C=1>ClCCl>[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18](=[O:23])/[CH:19]=[CH:20]/[CH2:21][CH3:22])[CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N+:3]=1[O-:32]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86691600(E)-1-[4-(2-Methyl-4-quinolyl)piperazin-1-yl]pent-2-en-1-one

Product 1

HCID 66835841(E)-1-[4-(2-Methyl-1-oxido-quinolin-1-ium-4-yl)piperazin-1-yl]pent-2-en-1-oneYield 18.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-1-[4-(2-Methyl-4-quinolyl)piperazin-1-yl]pent-2-en-1-one (30.9 mg, 0.1 mmol) was dissolved in anhydrous dichloromethane, meta-chloroperbenzoic acid (mCPBA) was added (44.6 mg, 0.2 mmol) and the mixture was stirred at room temperature for 15 minutes. The mixture was evaporated to dryness under reduced pressure and the residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 6 mg of a solid (0.0185 mmol, 18.5%). MS (APCI): m/z=325.8 [M+1]+.

Workup

  1. customThe mixture was evaporated to dryness under reduced pressure
  2. customthe residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)

Sources & evidence

ORD record
ord-f859c1cf3c8b4c32b6c3920f0971bb87
Source dataset
uspto-grants-2014_11
Patent number
US08883791B2

Reaction notes

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