Sodium Bicarbonate → N-(4-(1-aminoethyl)phenyl)methanesulfonamide

HRID 238931Notes

Reaction equation

HRID 238931 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[N:14]O)[CH3:13])=[CH:8][CH:7]=1)(=[O:4])=[O:3].[H][H].C([O-])(O)=O.[Na+]>[Pd].CO.Cl>[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([NH2:14])[CH3:13])=[CH:8][CH:7]=1)(=[O:4])=[O:3]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 6612326N-{4-[1-(hydroxyamino)ethylidene]cyclohexa-2,5-dien-1-ylidene}methanesulfonamideHCID 178418361HCID 178418361, compound

Product 1

HCID 16785149N-(4-(1-aminoethyl)phenyl)methanesulfonamideYield 99%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 4′-(Methylsulfonylamino)acetophenone oxime (13-8, 5 mmol) and 10% palladium on carbon (150 mg) in MeOH (25 mL) was treated with concentrated hydrochloric acid (10 drops) was hydrogenated under a balloon of hydrogen for 6 h. The reaction mixture was neutralized with solid NaHCO3, filtered and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using CH2Cl2:MeOH as eluant to afford 1-[4-(Methylsulfonylamino)phenyl]ethyl amine (13-11, LJO-302).

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-98d67a6b10e3498cb3044f613976c090
Source dataset
uspto-grants-2014_02
Patent number
US08642657B2

Reaction notes

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