Methylamine → 1-(3,4-Dimethoxyphenyl)-2-(methylamino)ethanone hydrobromide

HRID 428138Notes

Reaction equation

HRID 428138 reaction equation
[CH3:1][NH2:2].[Br:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH3:16])[CH:8]=1)=[O:6].ClCCl>C(O)(C)C>[BrH:3].[CH3:16][O:15][C:9]1[CH:8]=[C:7]([C:5](=[O:6])[CH2:4][NH:2][CH3:1])[CH:12]=[CH:11][C:10]=1[O:13][CH3:14]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 6344DichloromethaneHCID 2704232-Bromo-1-(3,4-dimethoxyphenyl)ethan-1-one

Product 1

HCID 183578301-(3,4-Dimethoxyphenyl)-2-(methylamino)ethanone hydrobromideYield 67%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

To isopropanol (200 ml), 40% aqueous methylamine solution (133 ml) was added and stirred under ice-cooling. 2-Bromo-1-(3,4-dimethoxyphenyl)ethanone (8.47 g, 33 mmol) was dissolved in isopropanol (10 ml) and dichloromethane (10 ml) and dropwise added to the reaction mixture over 1 hour. After the dropwise addition, the mixture was stirred for 15 minutes under ice-cooling. The solvent in the reaction mixture was distilled out at room temperature under reduced pressure and the precipitated crystal was filtered to yield 1-(3,4-dimethoxyphenyl)-2-(methylamino)ethanone hydrobromide (6.36 g, 67%).

Workup

  1. temperaturecooling
  2. additionAfter the dropwise addition
  3. stirringthe mixture was stirred for 15 minutes under ice-
  4. temperaturecooling
  5. distillationThe solvent in the reaction mixture was distilled out at room temperature under reduced pressure
  6. filtrationthe precipitated crystal was filtered

Sources & evidence

ORD record
ord-f19a693c76404b0d9266dbd4e2a1c7a7
Source dataset
uspto-grants-2001_11
Patent number
US06313153B1

Reaction notes

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