4-Methylamino-3-nitrobenzenesulfonic acid-n-methyl-n-(1-methylpiperidin-4-yl)amide → HCID 18412481, compound

HRID 50237Notes

Reaction equation

HRID 50237 reaction equation
[CH3:1][N:2]([CH:17]1[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]1)[S:3]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH3:13])=[C:8]([N+:14]([O-])=O)[CH:7]=1)(=[O:5])=[O:4].ClCCl.C(O)C>CO.[H][H].[Pd]>[CH3:1][N:2]([CH:17]1[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]1)[S:3]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH3:13])=[C:8]([NH2:14])[CH:7]=1)(=[O:5])=[O:4]

Participants

6

Reactant 2

HCID 184126614-Methylamino-3-nitrobenzenesulfonic acid-n-methyl-n-(1-methylpiperidin-4-yl)amideHCID 21584144Dichloromethane ethanol

Product 1

HCID 18412481HCID 18412481, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

1.5 g (4.4 mmol) of 4-methylamino-3-nitrobenzenesulfonic acid-N-methyl-N-(1-methylpiperidin-4-yl)amide were dissolved in 100 mL methanol and catalytically hydrogenated at room temperature and under 5 bar hydrogen pressure (10% palladium on charcoal). Then the catalyst was filtered off and the filtrate was evaporated down. The resulting oily product was further reacted without any purification. Yield: 1.4 g (100% of theory), C14H24N4O2S (312.4); Rf value: 0.33 (silica gel; dichloromethane/ethanol=4:1).

Workup

  1. filtrationThen the catalyst was filtered off
  2. customthe filtrate was evaporated down
  3. customThe resulting oily product was further reacted without any purification

Sources & evidence

ORD record
ord-764f1c61911a49cca01da460a75300f3
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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