Methylamine → N-{4-[1-hydroxy-2-(methylamino)ethyl]phenyl}acetamide

HRID 23694Notes

Reaction equation

HRID 23694 reaction equation
Br[CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=1)[OH:4].[CH3:15][NH2:16]>>[OH:4][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=1)[CH2:2][NH:16][CH3:15]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 22563212N-[4-(2-bromo-1-hydroxyethyl)phenyl]acetamide

Product 1

HCID 10171338N-{4-[1-hydroxy-2-(methylamino)ethyl]phenyl}acetamide

Procedure

To a solution of N-[4-(2-bromo-1-hydroxyethyl)phenyl]acetamide (0.40 g, in 10 mL of methanol) was introduced methylamine (10 mL, 2.0 M in methanol) at 0° C. The reaction mixture was warmed to room temperature after 30 minutes, and stirred at that temperature for 2 hours. The solvent and excess methylamine was evaporated. The residue was dissolved in methanol (5 mL) and stirred with resin (BioRad 50W×2, 0.5 g) overnight. The resin was collected by filtration, washed with methanol. The product on the resin was washed off with NH4OH/CH3OH (10% NH4OH aqueous solution (Aldrich, 29.4% NH3) in methanol, v/v). The solution was concentrated to give the title compound as a white solid (0.16 g).

Workup

  1. customThe solvent and excess methylamine was evaporated
  2. dissolutionThe residue was dissolved in methanol (5 mL)
  3. stirringstirred with resin (BioRad 50W×2, 0.5 g) overnight
  4. filtrationThe resin was collected by filtration
  5. washwashed with methanol
  6. washThe product on the resin was washed off with NH4OH/CH3OH (10% NH4OH aqueous solution (Aldrich, 29.4% NH3) in methanol, v/v)
  7. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-c9b7f9ee5af54c818ee459bf21884d38
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Reaction notes

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