Cis-3,5-dimethyl-1-(4-nitro-phenylmethanesulfonyl)-piperazine → 4-(Cis-3,5-dimethyl-piperazine-1-sulfonylmethyl)-phenylamine

HRID 1190118Notes

Reaction equation

HRID 1190118 reaction equation
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([S:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)(=[O:11])=[O:10])[CH2:3]1>CO.[Pd]>[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([S:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)(=[O:11])=[O:10])[CH2:3]1

Participants

4

Reactant 1

HCID 58994592Cis-3,5-dimethyl-1-(4-nitro-phenylmethanesulfonyl)-piperazine

Product 1

HCID 589944454-(Cis-3,5-dimethyl-piperazine-1-sulfonylmethyl)-phenylamineYield 105%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 298 mg (0.951 mmol) of cis-3,5-dimethyl-1-(4-nitro-phenylmethanesulfonyl)-piperazine (as prepared in the previous step) in MeOH (15 mL) was treated with 20 mg of 10% Pd/C (Degussa type E101-NE/W, Aldrich, 50% by weight water) and H2 (1 atm) at RT for 18 h. The mixture was filtered through Celite, and the filter cake was washed with MeOH. The solvent was removed in vacuo to afford 283 mg (100%) the title compound as an off-white solid: 1H-NMR (CDCl3; 400 MHz): δ 7.14 (d, 2H, J=8.4 Hz), 6.66 (d, 2H, J=8.4 Hz), 4.08 (s, 2H), 3.75 (br s, 2H), 3.52-3.50 (m, 1H), 3.48 (s, 4H), 2.88-2.76 (m, 2H), 2.23-2.15 (m, 2H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe filter cake was washed with MeOH
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-153af94f5451448e9e6581354b6831a4
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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