1-(2-Methoxy-5-nitrophenyl)-4-[2-(methylsulfonyl)ethyl]piperazine → HCID 59511390, compound

HRID 1157604Notes

Reaction equation

HRID 1157604 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[N:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH2:14][CH2:13]1>CCO.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[N:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][S:20]([CH3:23])(=[O:21])=[O:22])[CH2:14][CH2:13]1

Participants

4

Reactant 1

HCID 595114221-(2-Methoxy-5-nitrophenyl)-4-[2-(methylsulfonyl)ethyl]piperazine

Product 1

HCID 59511390HCID 59511390, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 0.5 g of 1-[2-(methyloxy)-5-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperazine (0.5 g, 1.46 mmol) in EtOH (15 mL) was added 10% Pd/C (0.05 g) and reaction stirred under H2 for 18 h. Reaction was then filtered through celite and the solvent removed in vacuo to give the desired product as yellow oil, 0.36 g (55% yield). 1H NMR (400 MHz, DMSO-D6) δ ppm 2.5 (m, 3H) 2.7 (t, J=6.4 Hz, 3H) 2.9 (d, J=1.8 Hz, 2H) 2.9 (d, J=11.4 Hz, 2H) 3.0 (s, 4H) 3.3 (d, J=6.4 Hz, 3H) 3.6 (s, 3H) 6.1 (dd, J=8.3, 2.5 Hz, 1H) 6.2 (d, J=2.4 Hz, 1H) 6.6 (d, J=8.8 Hz, 1H).

Workup

  1. customReaction
  2. filtrationwas then filtered through celite
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-d91ad7212af44843a622c333be636d69
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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