Ethyl bromoacetate → ethyl 2-(N-phenyl-N-propylamino)acetate

HRID 1608784Notes

Reaction equation

HRID 1608784 reaction equation
[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:2][CH3:3].Br[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>O1CCOCC1.C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1.O>[C:5]1([N:4]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:1][CH2:2][CH3:3])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 2

HCID 7748Ethyl bromoacetateHCID 12153Benzenamine, N-propyl-

Product 1

HCID 14060107ethyl 2-(N-phenyl-N-propylamino)acetateYield 90%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 312751,4-DioxaneSolventHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-eneSolvent

Procedure

To a solution of N-propylaniline (60 g) and ethyl bromoacetate (83.6 ml) in dioxane (60 ml), diazabicycloundecene (DBU;113 ml) was added dropwise under ice-cooling. After stirring for 1 hour at room temperature, the reaction mixture was diluted with water and extracted three times with ethyl acetate. The combined organic layer was washed with successive, 1N hydrochloric acid, water and saturated sodium chloride in order. After drying over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure to give 87.9 g (90%) of the objective compound.

Workup

  1. temperaturecooling
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic layer was washed with successive, 1N hydrochloric acid, water and saturated sodium chloride in order
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5d3693bbb8d0495b89f894c71e0141db
Source dataset
uspto-grants-1995_03
Patent number
US05397781

Reaction notes

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