Ammonia → 4-(4-Methanesulfonyl-piperazin-1-yl)-phenylamine

HRID 1795323Notes

Reaction equation

HRID 1795323 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([S:16]([CH3:19])(=[O:18])=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.N>CO.[Pd]>[CH3:19][S:16]([N:13]1[CH2:12][CH2:11][N:10]([C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:15][CH2:14]1)(=[O:17])=[O:18]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 2834838ST088463

Product 1

HCID 9419144-(4-Methanesulfonyl-piperazin-1-yl)-phenylamineYield 27.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

4-(4-Nitrophenyl)-1-methylsulfonylpiperazine (3.83 g, 13.4 mmol), as prepared in Reference Example 12a above, was mixed in methanol (100 ml) and 2 M ammonia in methanol (50 ml) and 10% palladium on carbon (400 mg) was added. The mixture was hydrogenated on a Paar apparatus (50 psi) for 3 h. The reaction was allowed to cool, the catalyst was filtered, washed with methanol then washed with chloroform. The chloroform portion contained a minor amount of the desired but looked purer. The chloroform portion was concentrated in vacuo and was recrystallized ethyl acetate to give 4-[4-(methylsulfonyl)-1-piperazinyl]benzenamine as a shiny brown solid (0.94 g, 27% yield, mp 192–193° C.). GC/MS (EI, M+) m/z=255.

Workup

  1. temperatureto cool
  2. filtrationthe catalyst was filtered
  3. washwashed with methanol
  4. washthen washed with chloroform
  5. concentrationThe chloroform portion was concentrated in vacuo
  6. customwas recrystallized ethyl acetate

Sources & evidence

ORD record
ord-d2e29cf5e44d423fb43e16e2c342e894
Source dataset
uspto-grants-2006_04
Patent number
US07026314B2

Reaction notes

Loading…