Ethyl Acetate → 4-(4-Biphenylylmethoxy)phenyl-N-[2-(N,N-dimethylamino)ethyl]acetamide

HRID 1356461Notes

Reaction equation

HRID 1356461 reaction equation
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16](OC)=[O:17])=[CH:11][CH:10]=2)=[CH:3][CH:2]=1.[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29][NH2:30].N1C=NC=N1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[C:1]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([NH:30][CH2:29][CH2:28][N:27]([CH3:31])[CH3:26])=[O:17])=[CH:11][CH:10]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 92571H-1,2,4-TriazoleHCID 66053N,N-DimethylethylenediamineHCID 18508368Methyl 4-(4-biphenylylmethoxy)phenylacetate

Product 1

HCID 99102684-(4-Biphenylylmethoxy)phenyl-N-[2-(N,N-dimethylamino)ethyl]acetamideYield 102.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of methyl 4-(4-biphenylylmethoxy)phenylacetate (60.0 g), N,N-dimethylethylenediamine (47.7 g), and 1H-1,2,4-triazole (12.6 g) in toluene (120 ml) was stirred under nitrogen at 100° C. for 8 hr and cooled until the temperature of the reaction mixture was reached to 60±2° C., to which ethyl acetate (240 ml) was added for 20 min. The reaction mixture was further heated under reflux for additional 30 min, left to stand at room temperature over night and stirred in an ice bath for 2 hr. The precipitate was collected by filtration and washed with ethyl acetate (120 ml) to obtain the titled compound (71.7 g).

Workup

  1. temperaturecooled until the temperature of the reaction mixture
  2. additionwas added for 20 min
  3. temperatureThe reaction mixture was further heated
  4. temperatureunder reflux for additional 30 min
  5. waitleft
  6. waitto stand at room temperature over night
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with ethyl acetate (120 ml)

Sources & evidence

ORD record
ord-308277ab1f71480a8c53ba4126813c84
Source dataset
uspto-grants-2003_07
Patent number
US06586475B1

Reaction notes

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