4-Chloro-3-nitrobenzenesulfonamide → HCID 67126453, compound

HRID 1848846Notes

Reaction equation

HRID 1848846 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.Cl[C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH2:25])(=[O:24])=[O:23])=[CH:18][C:17]=1[N+:26]([O-:28])=[O:27].C(N(CC)CC)C>O1CCOCC1>[C:11]([O:10][C:8]([N:5]1[CH2:4][CH2:3][CH:2]([NH:1][C:16]2[CH:21]=[CH:20][C:19]([S:22](=[O:23])(=[O:24])[NH2:25])=[CH:18][C:17]=2[N+:26]([O-:28])=[O:27])[CH2:7][CH2:6]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 73244-Chloro-3-nitrobenzenesulfonamideHCID 8471TriethylamineHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 67126453HCID 67126453, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Tert-butyl 4-aminopiperidine-1-carboxylate (8.63 g) was dissolved in 1,4-dioxane (250 mL), and 4-chloro-3-nitrobenzenesulfonamide (6.00 g) was added followed by triethylamine (10.60 mL). The solution was heated at 90° C. for 20 hours and then cooled. The solvent was removed under vacuum, and the material purified by flash column chromatography on silica gel using 50% ethyl acetate in hexanes, increasing to 100% ethyl acetate and increasing further to 20% methanol in dichloromethane.

Workup

  1. temperaturecooled
  2. customThe solvent was removed under vacuum
  3. customthe material purified by flash column chromatography on silica gel using 50% ethyl acetate in hexanes
  4. temperatureincreasing to 100% ethyl acetate
  5. temperatureincreasing further to 20% methanol in dichloromethane

Sources & evidence

ORD record
ord-462f528d26794f2d80e0f9833e5cc196
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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