2-Chloro-N,N-dimethylethylamine → 2-(3-(benzyloxy)phenoxy)-N,N-dimethylethanamine

HRID 1848818Notes

Reaction equation

HRID 1848818 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:17][CH2:18][N:19]([CH3:21])[CH3:20].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C.[OH-].[Na+]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[O:15][CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 10796Cesium carbonateHCID 138048Benzyl 3-hydroxyphenyl ether

Product 1

HCID 594475752-(3-(benzyloxy)phenoxy)-N,N-dimethylethanamine

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 3-(benzyloxy)phenol (2.002 g), 2-chloro-N,N-dimethylethanamine (1.459 g) in N,N-dimethylformamide (50 mL) was treated with cesium carbonate (3.91 g) and stirred at 50° C. overnight. The mixture was diluted with ethyl acetate and 1N aqueous NaOH and the layers were separated. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (5% 7N NH3 in methanol-dichloromethane) to give the desired product.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (5% 7N NH3 in methanol-dichloromethane)

Sources & evidence

ORD record
ord-5946aa963d364b3fb2baf7e602312d27
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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