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

HRID 624340Notes

Reaction equation

HRID 624340 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 NH; 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 NH; in methanol-dichloromethane)

Sources & evidence

ORD record
ord-b080b29fbf0340c5b64a3c030870d7f6
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

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