2-Amino-4-chlorophenol → N-[2-(2-Amino-4-chlorophenoxy)ethyl]-N,N-dimethylamine

HRID 1270135Notes

Reaction equation

HRID 1270135 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:18][CH2:19][N:20]([CH3:22])[CH3:21]>CC(C)=O>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([O:9][CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])=[C:2]([NH2:1])[CH:7]=1

Participants

5

Reactant 3

HCID 72652-Amino-4-chlorophenolHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 18449144N-[2-(2-Amino-4-chlorophenoxy)ethyl]-N,N-dimethylamineYield 74.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 2-Amino-4-chloro-phenol (1.43 g, 10 mmoles, 1 eq) and potassium carbonate (6.9 g, 50 mmoles, 5 eq) in acetone (25 ml) was added in one portion (2-Chloro-ethyl)-dimethyl-amine hydrochloride (2.16 g, 15 mmoles, 1.5 eq). The reaction mixture was refluxed under Nitrogen for 6 hours at which time the suspension was filtered and the solid washed with acetone. The combined filtrate was concentrated under vacuum and purified by flash chromatography (EtOAc/MeOH/NEt3: 87/9/3) to afford a beige solid (1.6 g, yield=72%).

Workup

  1. temperatureThe reaction mixture was refluxed under Nitrogen for 6 hours at which time the suspension
  2. filtrationwas filtered
  3. washthe solid washed with acetone
  4. concentrationThe combined filtrate was concentrated under vacuum
  5. custompurified by flash chromatography (EtOAc/MeOH/NEt3: 87/9/3)

Sources & evidence

ORD record
ord-c60a6dfebf5e488ba184fbb478e7b295
Source dataset
uspto-grants-2007_04
Patent number
US07202244B2

Reaction notes

Loading…