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

HRID 573052
Notes
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Reaction equation

HRID 573052 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 6228DimethylformamideSolvent
HCID 8857
Ethyl Acetate
Solvent
HCID 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-034151b1331a4c608ec883ea14fc4e6a
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09029404B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes