Water → [2-(4-Benzyloxyphenoxy)ethyl]dimethylamine

HRID 133771Notes

Reaction equation

HRID 133771 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:17][N:18]([CH3:22])[CH2:19][CH2:20]Cl.[H-].[Na+].O>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:20][CH2:19][N:18]([CH3:22])[CH3:17])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7638MonobenzoneHCID 24758Sodium hydrideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 59447665[2-(4-Benzyloxyphenoxy)ethyl]dimethylamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
90 °C

Procedure

4-(Benzyloxy)phenol (2.89 g, 0.01443 mol) in dimethylformamide (15 ml) and 2-(dimethylamino)ethyl chloride hydrochloride (2.32 g, 0.01611 mol) were added simultaneously in small portions to a 55-65% sodium hydride dispersion in mineral oil (0.033 mol) in dimethylformamide (5 ml) at 0° C. Then the mixture was allowed to warm to 90° C., and stirring was continued for 1.5 h. The cooled mixture was poured into water. The resultant mixture was extracted with toluene. The combined extracts were washed with 2.5 M NaOH and water and dried over Na2SO4. Toluene was evaporated and the residual product was used as such in the next step.

Workup

  1. extractionThe resultant mixture was extracted with toluene
  2. washThe combined extracts were washed with 2.5 M NaOH and water
  3. dry with materialdried over Na2SO4
  4. customToluene was evaporated

Sources & evidence

ORD record
ord-4ca4431bf066407e882feaaa0ee348f4
Source dataset
uspto-grants-2008_06
Patent number
US07390923B2

Reaction notes

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