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

HRID 1508054Notes

Reaction equation

HRID 1508054 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-efecc73992bd48cab6cab464bee51ae5
Source dataset
uspto-grants-2015_12
Patent number
US09221797B2

Reaction notes

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