Dimethylamine → 1-(2,5-Dimethoxyphenyl)-2-(dimethylamino)ethanone

HRID 620076Notes

Reaction equation

HRID 620076 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[O:13][CH3:14])=[O:4].[CH3:15][NH:16][CH3:17]>C1(C)C=CC=CC=1>[CH3:14][O:13][C:6]1[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:5]=1[C:3](=[O:4])[CH2:2][N:16]([CH3:17])[CH3:15]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 709972-Bromo-2',5'-dimethoxyacetophenone

Product 1

HCID 133020451-(2,5-Dimethoxyphenyl)-2-(dimethylamino)ethanone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-bromo-1-(2,5-dimethoxyphenyl)-ethanone (10.0 g) is added dropwise to a solution of dimethylamine (6.1 g) in toluene (450 ml). The mixture is stirred overnight at room temperature and extracted with a 1-N water solution of hydrochloric acid (3×250 ml). The mixed aqueous phases are alcalinized with a 25% water solution of sodium hydroxide (200 ml) and extracted with dichloromethane (4×250 ml). The mixed organic phases are washed with water (3×200 ml) and dried over magnesium sulphate. The solvent is distilled in vacuo and the residue is dried in vacuo to constant weight to give 1-(2,5-dimethoxyphenyl)-2-dimethylamino-ethanone which is a liquid, b.p. 250°-255°.

Workup

  1. extractionextracted with a 1-N water solution of hydrochloric acid (3×250 ml)
  2. extractionextracted with dichloromethane (4×250 ml)
  3. washThe mixed organic phases are washed with water (3×200 ml)
  4. dry with materialdried over magnesium sulphate
  5. distillationThe solvent is distilled in vacuo
  6. customthe residue is dried in vacuo to constant weight

Sources & evidence

ORD record
ord-364a082b1e0442ec88572e1cceb6faa6
Source dataset
uspto-grants-1989_04
Patent number
US04818765

Reaction notes

Loading…