Trifluoroacetic acid → N-(2-(2-(methylamino)ethyl)phenyl)methanesulfonamide

HRID 650824Notes

Reaction equation

HRID 650824 reaction equation
FC(F)(F)C(O)=O.C(O[C:13](=O)[N:14]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24][S:25]([CH3:28])(=[O:27])=[O:26])C)(C)(C)C.C(=O)([O-])O.[Na+]>ClCCl>[CH3:13][NH:14][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24][S:25]([CH3:28])(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium Bicarbonate2×HCID 20677519N-(2-(2-(methylsulfonylamino)phenyl)ethyl)-N-methylcarbamic acid tert-butyl ester

Product 1

HCID 10561338N-(2-(2-(methylamino)ethyl)phenyl)methanesulfonamideYield 51.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At 0° C., trifluoroacetic acid (6 ml) was added to a solution of N-(2-(2-(methylsulfonylamino)phenyl)ethyl)-N-methylcarbamic acid tert-butyl ester (870 mg, 2.6 mmol) in dichloromethane (6 ml). The reaction mixture was stirred for 50 min. Dichloromethane (24 ml) was added. A saturated aqueous solution of sodium hydrogen carbonate (34 ml) was added. Solid sodium hydrogen carbonate was added, until pH 7 was obtained. The phases were separated. The aqueous phase was extracted with dichloromethane (3×50 ml). The combined organic layers were dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash crhomatography on silica (60 g), using dichloromethane/methanol/25% aqueous ammonia (100:10:1) as eluent to give 308 mg of N-(2-(2-(methylamino)ethyl)phenyl)methanesulfonamide.

Workup

  1. customwas obtained
  2. customThe phases were separated
  3. extractionThe aqueous phase was extracted with dichloromethane (3×50 ml)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customThe crude product was purified by flash crhomatography on silica (60 g)

Sources & evidence

ORD record
ord-7728c890650447bdbdef7479c615b0c3
Source dataset
uspto-grants-2001_08
Patent number
US06274584B1

Reaction notes

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