2-Chloro-N,N-dimethylethylamine → [2-(3-Bromophenoxy)ethyl]dimethylamine

HRID 1798515Notes

Reaction equation

HRID 1798515 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Cl[CH2:10][CH2:11][N:12]([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:10][CH2:11][N:12]([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 11430Potassium CarbonateHCID 115633-Bromophenol

Product 1

HCID 413371[2-(3-Bromophenoxy)ethyl]dimethylamine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

3-Bromophenol (1 eq, 1.156 mmol, 0.2 g), 2-chloro-N,N-dimethylethanamine (1.1 eq, 1.272 mmol, 0.137 g) and potassium carbonate (3 eq, 3.47 mmol, 0.479 g) are mixed together in NMP (5 ml). The reaction mixture is heated at 80° C. for 6 hrs. The reaction mixture is dissolved in EtOAC and washed with water. The organic layer is washed with brine, dried over drying agent MgSO4, filtered and the organic solvent is reduced in vacuo to afford [2-(3-Bromo-phenoxy)-ethyl]-dimethyl-amine; [M+H]+ 245/247

Workup

  1. dissolutionThe reaction mixture is dissolved in EtOAC
  2. washwashed with water
  3. washThe organic layer is washed with brine
  4. customdried
  5. dry with materialover drying agent MgSO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-c9ee98ba70c741c8921d3c5f38caa33b
Source dataset
uspto-grants-2013_01
Patent number
US08343966B2

Reaction notes

Loading…