Formic Acid → (Methylsulfonyl)(2-Piperazinylphenyl)Amine

HRID 1419584Notes

Reaction equation

HRID 1419584 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+].C(O)=O>CO.[Pd]>[N:11]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 2723923Ammonium formateHCID 21935090N-[2-(4-Benzylpiperazin-1-yl)phenyl]methanesulfonamide

Product 1

HCID 19261360(Methylsulfonyl)(2-Piperazinylphenyl)AmineYield 57.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of the product of N-[2-(4-benzylpiperazin-1-yl)phenyl]methanesulfonamide (2.83 g, 8.2 mmol) in methanol (40 mL) was purged with nitrogen (0.25 hour). Ammonium formate (1.55 g, 24.6 mmol), formic acid (0.31 mL, 8.21 mmol) and palladium on activated charcoal (0.5 g) were added. The mixture was heated at reflux for 2 h., cooled, filtered, and the solvent was evaporated under reduced pressure. The residue was diluted with ethyl acetate and washed with aqueous potassium carbonate (saturated, 3×). The organic layer was dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a pale yellow crystalline solid (1.196 g, 57%), δH (250 MHz, CDCl3) 7.52 (1H, dd, J 1.6, 8.0 Hz), 7.23-7.05 (4H, m), 3.06 (3H, s), 3.06-3.02 (4H, m), 2.85-2.78 (4H, m), and 1.80 (1H, br s).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h.
  3. temperaturecooled
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. additionThe residue was diluted with ethyl acetate
  7. washwashed with aqueous potassium carbonate (saturated, 3×)
  8. dry with materialThe organic layer was dried (MgSO4)
  9. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a34deda780f242f498bc06847e78f63a
Source dataset
uspto-grants-1999_03
Patent number
US05885999

Reaction notes

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