Ammonium formate → 4-[N-(2-Hydroxy-3-piperidinopropyl)sulphamoyl]aniline

HRID 1071947Notes

Reaction equation

HRID 1071947 reaction equation
C([O-])=O.[NH4+].[OH:5][CH:6]([CH2:21][N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:7][NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)(=[O:11])=[O:10]>[Pd].C(O)C>[OH:5][CH:6]([CH2:21][N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:7][NH:8][S:9]([C:12]1[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=1)(=[O:10])=[O:11]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 223906864-[N-(2-Hydroxy-3-piperidinopropyl)sulphamoyl]nitrobenzene

Product 1

HCID 223905914-[N-(2-Hydroxy-3-piperidinopropyl)sulphamoyl]anilineYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

Ammonium formate (1.1 g, 17.46 mmol) followed by a slurry of 10% palladium on carbon catalyst (0.7 g) in ethanol was added in portions to a suspension of 4-[N-(2-Hydroxy-3-piperidinopropyl)sulphamoyl]nitrobenzene (Method 117; 1.2 g, 3.5 mmol) in ethanol (100 ml). The mixture was heated at reflux under nitrogen for 2 hours. The mixture was cooled and the catalyst was removed by filtration through diatomaceous earth. The filter pad was washed with ethanol and the combined filtrates were evaporated. The residue was triturated with diethyl ether, collected by filtration and dried, to give the title compound (0.93 g, 85%) as a pale green solid. NMR: 1.3-1.5 (m, 6H), 2.10-2.32 (m, 6H), 2.60 (m, 1H), 2.75 (m, 1H), 3.52 (m, 1H), 4.50 (brs, 1H), 5.85 (s, 2H), 6.59 (d, 2H), 6.98 (brs, 1H), 7.39 (d, 2H); m/z: 314.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux under nitrogen for 2 hours
  3. temperatureThe mixture was cooled
  4. customthe catalyst was removed by filtration through diatomaceous earth
  5. washThe filter pad was washed with ethanol
  6. customthe combined filtrates were evaporated
  7. customThe residue was triturated with diethyl ether
  8. filtrationcollected by filtration
  9. customdried

Sources & evidence

ORD record
ord-9368b027c5f44e5aba3bcfe42575fdc3
Source dataset
uspto-grants-2005_06
Patent number
US06908920B2

Reaction notes

Loading…