N-[4-([1-(4-nitro-2-pyridyl)piperidin-4-yl]methoxy)phenyl]methanesulphonamide → N-[4-([1-(4-Amino-2-pyridyl)piperidin-4-yl]methoxy)phenyl]methanesulphonamide

HRID 345437Notes

Reaction equation

HRID 345437 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][CH:19]=3)[CH2:12][CH2:11]2)[CH:5]=1)([O-])=O>C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([N:10]2[CH2:11][CH2:12][CH:13]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][CH:19]=3)[CH2:14][CH2:15]2)[CH:5]=1

Participants

3

Reactant 1

HCID 19992415N-[4-([1-(4-nitro-2-pyridyl)piperidin-4-yl]methoxy)phenyl]methanesulphonamide

Product 1

HCID 19992427N-[4-([1-(4-Amino-2-pyridyl)piperidin-4-yl]methoxy)phenyl]methanesulphonamideYield 92.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-[4-([1-(4-nitro-2-pyridyl)piperidin-4-yl]methoxy)phenyl]methanesulphonamide (see Preparation 5) (140 mg) in ethanol (50 ml) was hydrogenated at room temperature and 3.5 bar in the presence of 5% palladium on carbon until the required amount of hydrogen had been absorbed. The catalyst was filtered off and the filtrate was evaporated to give the product (120 mg), m.p. 213°-214° (from ethyl acetate/methanol).

Workup

  1. customwas hydrogenated at room temperature
  2. custom3.5 bar in the presence of 5% palladium on carbon until the required amount of hydrogen had been absorbed
  3. filtrationThe catalyst was filtered off
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-fc52c9c135ce4bacbf73adfbb7d451e5
Source dataset
uspto-grants-1991_10
Patent number
US05057528

Reaction notes

Loading…