4-Chloro-3-nitrobenzenesulfonamide → 4-[1-(2-Methoxy-ethyl)-piperidin-4-ylamino]-3-nitro-benzenesulfonamide

HRID 629599

Reaction equation

HRID 629599 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([NH2:11])[CH2:7][CH2:6]1.C(N(CC)CC)C.Cl[C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH2:29])(=[O:28])=[O:27])=[CH:22][C:21]=1[N+:30]([O-:32])=[O:31]>O1CCOCC1>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([NH:11][C:20]2[CH:25]=[CH:24][C:23]([S:26]([NH2:29])(=[O:28])=[O:27])=[CH:22][C:21]=2[N+:30]([O-:32])=[O:31])[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 73244-Chloro-3-nitrobenzenesulfonamideHCID 8471TriethylamineHCID 201191211-(2-Methoxyethyl)piperidin-4-amine

Product 1

HCID 684066134-[1-(2-Methoxy-ethyl)-piperidin-4-ylamino]-3-nitro-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

1-(2-Methoxy-ethyl)-piperidin-4-ylamine (2.01 g) and triethylamine (3.24 mL, 2.35 g) were added to 1,4-dioxane (60 mL). 4-Chloro-3-nitrobenzenesulfonamide (2.50 g) was added, and the mixture was heated to 90° C. for 16 hours. The mixture was cooled and the material purified by flash column chromatography on silica gel using 10% methanol in dichloromethane.

Workup

  1. temperatureThe mixture was cooled
  2. customthe material purified by flash column chromatography on silica gel using 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-1158022bd4ec41c8aca24c74d2ca769e
Source dataset
uspto-grants-2016_04
Patent number
US09315488B2

Linked notes

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