Ethyl 2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]benzoate → 1-(4-ethoxy-3-formylphenylsulfonyl)-4-methylpiperazine

HRID 1581739Notes

Reaction equation

HRID 1581739 reaction equation
[CH2:1]([O:3][C:4]1[CH:14]=[CH:13][C:12]([S:15]([N:18]2[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]2)(=[O:17])=[O:16])=[CH:11][C:5]=1[C:6](OCC)=[O:7])[CH3:2]>O=[Mn]=O>[CH2:1]([O:3][C:4]1[CH:14]=[CH:13][C:12]([S:15]([N:18]2[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]2)(=[O:16])=[O:17])=[CH:11][C:5]=1[CH:6]=[O:7])[CH3:2]

Participants

3

Reactant 1

HCID 22052241Ethyl 2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]benzoate

Product 1

HCID 98397651-(4-ethoxy-3-formylphenylsulfonyl)-4-methylpiperazineYield 47.4%

Reagents, catalysts & solvents 1

HCID 14801Manganese dioxideCatalyst

Procedure

MnO2 (100 g, 1.15 mol) was loaded into a flask, followed by 1-(4-ethoxy-3-hydroxymethylphenylsulfonyl)-4-methylpiperazine (15 g, 0.05 mol, from step (b) above). This was washed with acetone (150 mL) and the suspension stirred for 3 hours. The MnO2 was filtered off onto Celite® and the filtrate concentrated under vacuum to give a pale yellow oil. This was recrystallised from toluene to give the title compound as a pale green solid (7.4 g, 47%).

Workup

  1. washThis was washed with acetone (150 mL)
  2. filtrationThe MnO2 was filtered off onto Celite®
  3. concentrationthe filtrate concentrated under vacuum
  4. customto give a pale yellow oil
  5. customThis was recrystallised from toluene

Sources & evidence

ORD record
ord-d3196747ca41476fafde0a110ee2bd5b
Source dataset
uspto-grants-2004_05
Patent number
US06730786B2

Reaction notes

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