N-(1-benzylpiperidin-4-yl)-2-nitro-4-methylsulphonylaniline → N-(1-benzylpiperidin-4-yl)-2-amino-4-methylsulphonylaniline

HRID 1592996Notes

Reaction equation

HRID 1592996 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][C:16]=2[N+:25]([O-])=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][C:16]=2[NH2:25])[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 9281505N-(1-benzylpiperidin-4-yl)-2-nitro-4-methylsulphonylaniline

Product 1

HCID 68704672N-(1-benzylpiperidin-4-yl)-2-amino-4-methylsulphonylanilineYield 84.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

The crude material from step 1 (170 g) was dissolved in 3 litres of methanol in a pressure vessel, 20 g of moist 5% Pd/C catalyst was added and stirred under an atmosphere of hydrogen at 3 bar and 50° C. for one hour. The reaction was cooled, filtered and evaporated to give 133 g N-(1-benzylpiperidin-4-yl)-2-amino-4-methylsulphonylaniline as a brown solid.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. customevaporated

Sources & evidence

ORD record
ord-cc1fcd5e26f745c7890f5317bdfd005f
Source dataset
uspto-grants-2007_11
Patent number
US07294636B2

Reaction notes

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